Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid or a derivative thereof and auxin transport inhibitors

ABSTRACT

Provided herein are herbicidal composition containing and method of controlling undesirable vegetation utilizing (a) a compound of formula (I): 
                         
or an agriculturally acceptable salt or ester thereof and (b) an auxin transport inhibitor. Exemplary auxin transport inhibitors include chlorflurenol-methyl, diflufenzopyr, flurenol and naptalam, or an agriculturally acceptable derivative thereof. The methods and compositions described herein provide control of undesirable vegetation, e.g., in rice, cereals, wheat, barley, oats, rye, sorghum, corn or maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, vegetables, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crop, industrial vegetation management (IVM) or rights of way (ROW).

PRIORITY CLAIM

This application claims the benefit of U.S. provisional patentapplication No. 61/675,093 filed on Jul. 24, 2012, this provisionalapplication is incorporated herein by reference in its entirety.

FIELD

Provided herein are herbicidal compositions comprising (a)4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylicacid or an agriculturally acceptable ester or salt thereof and (b) anauxin transport inhibitor.

Provided herein are also methods of controlling undesirable vegetationcomprising applying (a)4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylicacid or an agriculturally acceptable ester or salt thereof and (b) anauxin transport inhibitor.

BACKGROUND

The protection of crops from weeds and other vegetation which inhibitcrop growth is a constantly recurring problem in agriculture. To helpcombat this problem, researchers in the field of synthetic chemistryhave produced an extensive variety of chemicals and chemicalformulations effective in the control of such unwanted growth. Chemicalherbicides of many types have been disclosed in the literature and alarge number are in commercial use. However, there remains a need forcompositions and methods that are effective in controlling undesirablevegetation.

SUMMARY

A first embodiment of the invention provided herein includes herbicidalcompositions comprising an herbicidally effective amount of (a) acompound of the formula (I)

or an agriculturally acceptable salt or ester thereof, and (b) at leastone auxin transport inhibitor.

A second embodiment includes the mixture of the first embodiment inwhich formula (I) is present in at least one of the following forms: acarboxylic acid, a carboxylate salt, an aralkyl, an alkyl ester, anunsubstituted benzyl, a substituted benzyl, a C₁₋₄ alkyl, and/or ann-butyl ester.

A third embodiment includes the mixture according to either the first orsecond embodiments wherein the (b) at least one auxin transportinhibitor is at least one compound selected from the group consistingof: chlorflurenol-methyl, chlorflurenol, diflufenzopyr, diflufenzopyrsodium, flurenol-methyl, flurenol, and naptalam, or an agriculturallyacceptable salt, carboxylic acid, carboxylate salt, or ester thereof ofat least one of the aforementioned auxin transport inhibitor.

A fourth embodiment includes the mixtures according to any of the first,second, or third embodiments in which the auxin transport inhibitor inthe mixture is chlorflurenol-methyl or chlorflurenol wherein the weightratio of the compound of formula (I) to chlorflurenol-methyl orchlorflurenol given in units of gae/ha to gai/ha or gae/ha to gae/ha isselected from the group of ranges of ratios and ratios consisting of:4.4:1, 1:3.9, 1:7.9, 1:15.7, 1:31.4, 1:62.8, 1:125.6, from 1:15.7 to1:62.8, 1:1680, from 1:3.9 to 1:62.8, from 1:7.9 to 1:62.8, from 1:15.7to 1:125.6, from 1:15.7 to 1:62.8, from 4.4:1 to about 1:1680, or withinany range defined between any pair of the foregoing values.

A fifth embodiment includes the mixtures according to any of the first,second, or third embodiments in which the auxin transport inhibitor. inthe mixture is diflufenzopyr or diflufenzopyr sodium wherein the weightratio of the compound of formula (I) to diflufenzopyr or diflufenzopyrsodium given in units of gae/ha to gai/ha or gae/ha to gae/ha isselected from the group of ranges of ratios and ratios consisting of:86:1, 2:1, 1.8:1, 1:1, 1:1.1, 1:2, 1:2.2, 1:4, 1:4.4, 1:8, 1:8.8, 1:18,from 2:1 to 1:4, from 2:1 to 1:8, from 1.8:1 to 1:8.8, from 1:1680 to4.4:1, or within any range defined between any pair of the foregoingvalues.

A sixth embodiment includes the mixtures according to any of the first,second, or third embodiments in which the auxin transport inhibitor inthe mixture is flurenol-methyl or flurenol wherein the weight ratio ofthe compound of formula (I) to flurenol-methyl or flurenol given inunits of gae/ha to gai/ha or gae/ha to gae/ha is selected from the groupof ranges of ratios and ratios consisting of: 4.4:1, 1:2.2, 1:4.3,1:8.6, 1:17.2, 1:34.4, from 1:8.6 to 1:34.4, 1:1680, from 1:2.2 to1:17.2, from 4.4:1 to 1:1680, or within any range defined between anypair of the foregoing values.

A seventh embodiment includes the mixtures according to any of thefirst, second, or third embodiments in which the auxin transportinhibitor in the mixture is naptalam wherein the weight ratio of thecompound of formula (I) to naptalam given in units of gae/ha to gai/haor gae/ha to gae/ha is selected from the group of ranges of ratios andratios consisting of: 2:1, 1.1:1, 1:1.9, 1:3.8, 1:7.5, 1:10.3, 1:15,1:20.6, 1:41.3, 1:82.5, 1:165, 1:2250, from 1:1.9 to 1:15, from 1.1:1 to1:15, from 1:10.31 to 1:165, from 2:1 to 1:2250, or within any rangedefined between any pair of the foregoing values.

An eighth embodiment includes any composition according to any of thefirst through the seventh embodiments wherein the mixture furthercomprises at least one an agriculturally acceptable agent selected fromthe group consisting of an adjuvant, a carrier, or a safener.

A ninth embodiment includes methods of controlling undesirablevegetation comprising the step of applying or otherwise contactingvegetation and/or soil, and/or water with a herbicidally effectiveamount of at least one mixture according to any of the first through theeighth embodiments.

A tenth embodiment includes methods according to the ninth embodimentwherein undesirable vegetation is controlled according to at leasttechnique selected from the group consisting of: direct-seeded,water-seeded, and/or transplanted rice, cereals, wheat, barley, oats,rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola,sugar beet, soybean, cotton, pineapple, pastures, grasslands,rangelands, fallowland, turf, tree and vine orchards, aquatics,plantation crops, vegetables, industrial vegetation management (IVM), orrights-of-way (ROW).

An eleventh embodiment includes methods according to either of the ninthand tenth embodiments wherein a herbicidally effective amount of themixture is applied either pre- or post-emergently to at least one of thefollowing: a crop, a field, a ROW, or a paddy.

A twelfth embodiment includes methods according to any of the ninththrough the eleventh embodiments wherein the undesirable vegetationcontrolled by an application of a herbicidally effective amount of themixture and at least one of the following phytotoxic actives:glyphosate-, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthaseinhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-,phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transportinhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-,phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-,imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-,triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactatesynthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-,4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-, phytoenedesaturase inhibitor-, carotenoid biosynthesis inhibitor-,protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesisinhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chainfatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-,photosystem I inhibitor-, photosystem II inhibitor-, protoporphyrinogenoxidase (PPO) inhibitor-, triazine-, or bromoxynil-tolerant crops.

A thirteenth embodiment includes a at least one method according to anyof the ninth through the twelfth embodiments wherein a plant that istolerant to at least one herbicide is treated, and where the tolerantcrop possesses multiple or stacked traits conferring tolerance tomultiple herbicides or inhibitors of multiple modes of action, in someembodiments the treated plant that expresses resistance to a herbicideis a itself undesirable vegetation.

A fourteenth embodiment includes methods according to the thirteenthembodiment, wherein the resistant or tolerant weed is a biotype withresistance or tolerance to multiple herbicides, multiple chemicalclasses, inhibitors of multiple herbicide modes-of-action, or viamultiple resistance mechanisms.

A fiftieth embodiment includes at least one of the methods according toeither the thirteenth of fourteenth embodiments, wherein the resistantor tolerant undesirable plant is a biotype resistant or tolerant to atleast on agent selected from the groups consisting of: acetolactatesynthase (ALS) inhibitors or acetohydroxy acid synthase (AHAS),photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors,synthetic auxins, auxin transport inhibitors, photosystem I inhibitors,5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors,microtubule assembly inhibitors, fatty acid and lipid synthesisinhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoidbiosynthesis inhibitors, very long chain fatty acid (VLCFA) inhibitors,phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors,4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors, mitosisinhibitors, cellulose biosynthesis inhibitors, herbicides with multiplemodes-of-action, quinclorac, arylaminopropionic acids, difenzoquat,endothall, or organoarsenicals.

A sixteenth embodiment includes methods of controlling undesirablevegetation comprising the step of applying a herbicidally effectiveamount of at least one mixture according to the fourth embodimentwherein the amount of the mixture is applied at a rate, expressed ingai/ha or gae/ha of chlorflurenol-methyl or chlorflurenol selected fromthe group of rates and ranges of rates consisting of, about: 68.75,137.5, 275, 550 or within any range defined between any pair of theforegoing values.

A seventeenth embodiment includes methods according to either of thefourth and sixteenth embodiments wherein the controlled plant is atleast one plant selected from the group consisting of: ECHCG, ECHCO,CYPIR, LEFCH, IPOHE, DIGSA, ECHOR, SCPMA, still other embodimentsinclude controlling plants from the genera consisting of: Echinochloa,Cyperus, Leptochloa, Ipomoea, Digitaria, Schoenoplectus, andBolboschoenus.

An eighteenth embodiment includes methods of controlling undesirablevegetation comprising the step of applying a herbicidally effectiveamount of at least one a mixture according to the fifth embodimentwherein the amount of the mixture is applied at a rate, expressed ingai/ha or gae/ha of diflufenzopyr or diflufenzopyr sodium selected fromthe group of rates and ranges of rates consisting of, about: 8.75, 17.5,35, 70, or within any range defined between any pair of the foregoingvalues.

A nineteenth embodiment includes methods according to either of thefifth and eighteenth embodiments wherein the controlled plant is atleast one plant selected from the group consisting of: BRAPP, LEFCH,DIGSA, IPOHE, ECHCG, CYPRO, FIMMI, still other embodiments includecontrolling plants from the genera consisting of: Brachiaria,Leptochloa, Digitaria, Ipomoea, Echinochloa, Cyperus, and Fimbristylis.

A twentieth embodiment includes methods of controlling undesirablevegetation comprising the step of applying a herbicidally effectiveamount of at least one a mixture according to the sixth embodimentwherein the amount of the mixture is applied at a rate, expressed ingai/ha or gae/ha of flurenol or flurenol-methyl selected from the groupof rates and ranges of rates consisting of, about: 68.75, 137.5, 275, orwithin any range defined between any pair of the foregoing values.

A twenty-first embodiment includes methods according to either of thesixth and twentieth embodiments wherein the controlled plant is at leastone plant selected from the group consisting of: BRAPP, CYPIR, ECHCG,FIMMI, CYPRO still other embodiments include controlling plants from thegenera consisting of: Brachiaria, Cyperus, Echinochloa, Fimbristylis,and Cyperus.

A twenty-second embodiment includes methods of controlling undesirablevegetation comprising the step of applying a herbicidally effectiveamount of at least one a mixture according to the seventh embodimentwherein the amount of the mixture is applied at a rate, expressed ingai/ha or gae/ha of naptalam selected from the group of rates and rangesof rates consisting of, about: 30, 60, 120, 330, 660, 1320, or withinany range defined between any pair of the foregoing values.

A twenty-third embodiment includes methods according to either of theseventh and twenty-second embodiments wherein the controlled plant is atleast one plant selected from the group consisting of: BRAPP, LEFCH,IPOHE, ECHCG, FIMMI, ECHOR, CYPRO, still other embodiments includecontrolling plants from the genera consisting of: Brachiaria,Leptochloa, Ipomoea, Echinochloa, Fimbristylis, Echinochloa, andCyperus.

Provided herein are herbicidal compositions comprising a herbicidallyeffective amount of (a) a compound of the formula (I)

or an agriculturally acceptable salt or ester of thereof, and (b) anauxin transport inhibitor. The compositions may also contain anagriculturally acceptable adjuvant or carrier.

Provided herein are also methods of controlling undesirable vegetationcomprising applying (a) a compound of formula (I) or an agriculturallyacceptable ester or salt thereof and (b) an auxin transport inhibitor.

DETAILED DESCRIPTION Definitions

As used herein, the compound of formula (I) has the following structure:

The compound of formula (I) can be identified by the name4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylicacid and has been described in U.S. Pat. No. 7,314,849 (B2), which isincorporated herein by reference in its entirety. Exemplary uses of thecompound of the formula (I) include controlling undesirable vegetation,including grass, broadleaf and sedge weeds, in multiple non-crop andcropping situations.

Without being limited to any theory, auxin transport inhibitorsinterfere with auxins' abilities to mediate plant growth anddevelopment. Exemplary auxin transport inhibitors include, but are notlimited to, chlorflurenol-methyl, diflufenzopyr, flurenol and naptalam,or salts or esters thereof.

As used herein, chlorflurenol-methyl is methyl2-chloro-9-hydroxy-9H-fluorene-9-carboxylate. Exemplary uses ofchlorflurenol-methyl are described in Tomlin, C., ed. A World CompendiumThe Pesticide Manual. 15^(th) ed. Alton: BCPC Publications, 2009(hereafter “The Pesticide Manual, Fifteenth Edition, 2009.”). Exemplaryuses of chlorflurenol-methyl include its use as a plant growth retardantand weed suppressant, e.g., in amenity grass, roadsides, railways, andditch banks. Chlorflurenol-methyl possesses the following structure:

As used herein, diflufenzopyr is2-{(E)-1-[4-(3,5-difluorophenyl)-semicarbazono]-ethyl}nicotinic acid.Exemplary uses of diflufenzopyr are described in The Pesticide Manual,Fifteenth Edition, 2009. Exemplary uses of diflufenzopyr include its usefor post-emergence control of annual broad-leaved and perennial weeds,e.g., in maize, pasture/rangeland and non-crop areas. Diflufenzopyrpossesses the following structure:

An exemplary diflufenzopyr form includes its acid and its sodium saltform, i.e., diflufenzopyr sodium.

As used herein, flurenol is 9-hydroxy-9H-fluorene-9-carboxylic acid.Exemplary uses of flurenol are described in The Pesticide Manual,Fifteenth Edition, 2009. Exemplary uses of flurenol include its use forpost-emergence control of broad-leaved weeds, e.g., in cereal grass andrice. Flurenol possesses the following structure:

An exemplary form of flurenol includes flurenol butyl,flurenol-dimethylammonium, and florenol-methyl.

As used herein, naptalam is 2-[(1-naphthalenylamino)carbonyl]benzoicacid. It is described in The Pesticide Manual, Fifteenth Edition, 2009.Naptalam possesses the following structure:

Exemplary forms of naptalam include its sodium salt.

As used herein, herbicide means a compound, e.g., active ingredient thatkills, controls or otherwise adversely modifies the growth of plants.

As used herein, a herbicidally effective or vegetation controllingamount is an amount of active ingredient which causes an adverselymodifying effect to the vegetation e.g., causing deviations from naturaldevelopment, killing, effecting regulation, causing desiccation, causingretardation, and the like.

As used herein, controlling undesirable vegetation means preventing,reducing, killing, or otherwise adversely modifying the development ofplants and vegetation. Described herein are methods of controllingundesirable vegetation through the application of certain herbicidecombinations or compositions. Methods of application include, but arenot limited to applications to the vegetation or locus thereof, e.g.,application to the area adjacent to the vegetation, as well aspre-emergence, post-emergence, foliar (broadcast, directed, banded,spot, mechanical, over-the-top, or rescue), and in-water applications(emerged and submerged vegetation, broadcast, spot, mechanical,water-injected, granular broadcast, granular spot, shaker bottle, orstream spray) via hand, backpack, machine, tractor, or aerial (airplaneand helicopter) application methods.

As used herein, plants and vegetation include, but are not limited to,germinant seeds, emerging seedlings, plants emerging from vegetativepropagules, immature vegetation, and established vegetation.

As used herein, agriculturally acceptable salts and esters refer tosalts and esters that exhibit herbicidal activity, or that are or can beconverted in plants, water, or soil to the referenced herbicide.Exemplary agriculturally acceptable esters are those that are or can behydrolyzed, oxidized, metabolized, or otherwise converted, e.g., inplants, water, or soil, to the corresponding carboxylic acid which,depending on the pH, may be in the dissociated or undissociated form.

Exemplary salts include those derived from alkali or alkaline earthmetals and those derived from ammonia and amines. Exemplary cationsinclude sodium, potassium, magnesium, and aminium cations of theformula:R¹R²R³R⁴N⁺wherein R¹, R², R³ and R⁴ each, independently represents hydrogen orC₁-C₁₂ alkyl, C₃-C₁₂ alkenyl or C₃-C₁₂ alkynyl, each of which isoptionally substituted by one or more hydroxy, C₁-C₄ alkoxy, C₁-C₄alkylthio or phenyl groups, provided that R¹, R², R³ and R⁴ aresterically compatible. Additionally, any two of R¹, R², R³ and R⁴together may represent an aliphatic difunctional moiety containing oneto twelve carbon atoms and up to two oxygen or sulfur atoms. Salts canbe prepared by treatment with a metal hydroxide, such as sodiumhydroxide, with an amine, such as ammonia, trimethylamine,diethanolamine, 2-methylthiopropylamine, bisallylamine,2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine orwith a tetraalkylammonium hydroxide, such as tetramethylammoniumhydroxide or choline hydroxide.

Exemplary esters include those derived from C₁-C₁₂ alkyl, C₃-C₁₂alkenyl, C₃-C₁₂ alkynyl or C₇-C₁₀ aryl-substituted alkyl alcohols, suchas methyl alcohol, isopropyl alcohol, 1-butanol, 2-ethylhexanol,butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol,cyclohexanol or unsubstituted or substituted benzyl alcohols. Benzylalcohols may be substituted with from 1-3 substituents independentlyselected from halogen, C₁-C₄ alkyl or C₁-C₄ alkoxy. Esters can beprepared by coupling of the acids with the alcohol using any number ofsuitable activating agents such as those used for peptide couplings suchas dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); byreacting the acids with alkylating agents such as alkylhalides oralkylsulfonates in the presence of a base such as triethylamine orlithium carbonate; by reacting the corresponding acid chloride of anacid with an appropriate alcohol; by reacting the corresponding acidwith an appropriate alcohol in the presence of an acid catalyst or bytransesterification.

Compositions and Methods

A first embodiment of the invention provided herein includes herbicidalcompositions comprising an herbicidally effective amount of (a) acompound of the formula (I)

or an agriculturally acceptable salt or ester thereof, and (b) at leastone auxin transport inhibitor.

A second embodiment includes the mixture of the first embodiment inwhich of formula (I), is present in the form of at least one of thefollowing forms: a carboxylic acid, a carboxylate salt, an aralkyl, analkyl ester, an unsubstituted benzyl, a substituted benzyl, a C₁₋₄alkyl, and/or an n-butyl ester.

A third embodiment includes the mixture according to either the first orsecond embodiments wherein the (b) at least one auxin transportinhibitor is at least one compound selected from the group consistingof: chlorflurenol-methyl, chlorflurenol, diflufenzopyr, diflufenzopyrsodium, flurenol-methyl, flurenol, and naptalam, or an agriculturallyacceptable salt, carboxylic acid, carboxylate salt, or ester thereof ofat least one of the aforementioned auxin transport inhibitor.

A fourth embodiment includes the mixtures according to any of the first,second, or third embodiments in which the auxin transport inhibitor inthe mixture is chlorflurenol-methyl or chlorflurenol wherein the weightratio of the compound of formula (I) to chlorflurenol-methyl orchlorflurenol given in units of gae/ha to gai/ha is selected from thegroup of ranges of ratios and ratios consisting of 4.4:1, 1:3.9, 1:7.9,1:15.7, 1:31.4, 1:62.8, 1:125.6, from 1:15.7 to 1:62.8, 1:1680, from1:3.9 to 1:62.8, from 1:7.9 to 1:62.8, from 1:15.7 to 1:125.6, from1:15.7 to 1:62.8, from 4.4:1 to about 1:1680, or within any rangedefined between any pair of the foregoing values.

A fifth embodiment includes the mixtures according to any of the first,second, or third embodiments in which the auxin transport inhibitor. inthe mixture is diflufenzopyr or diflufenzopyr sodium wherein the weightratio of the compound of formula (I) to diflufenzopyr or diflufenzopyrsodium given in units of gae/ha to gai/ha is selected from the group ofranges of ratios and ratios consisting of: 86:1, 2:1, 1.8:1, 1:1, 1:1.1,1:2, 1:2.2, 1:4, 1:4.4, 1:8, 1:8.8, 1:18, from 2:1 to 1:4, from 2:1 to1:8, from 1.8:1 to 1:8.8, from 1:1680 to 4.4:1, or within any rangedefined between any pair of the foregoing values.

A sixth embodiment includes the mixtures according to any of the first,second, or third embodiments in which the auxin transport inhibitor inthe mixture is flurenol-methyl or flurenol wherein the weight ratio ofthe compound of formula (I) to flurenol-methyl or flurenol given inunits of gae/ha to gai/ha is selected from the group of ranges of ratiosand ratios consisting of: 4.4:1, 1:2.2, 1:4.3, 1:8.6, 1:17.2, 1:34.4,from 1:8.6 to 1:34.4, 1:1680, from 1:2.2 to 1:17.2, from 4.4:1 to1:1680, or within any range defined between any pair of the foregoingvalues.

A seventh embodiment includes the mixtures according to any of thefirst, second, or third embodiments in which the auxin transportinhibitor in the mixture is naptalam wherein the weight ratio of thecompound of formula (I) to naptalam given in units of gae/ha to gai/hais selected from the group of ranges of ratios and ratios consisting of:2:1, 1.1:1, 1:1.9, 1:3.8, 1:7.5, 1:10.3, 1:15, 1:20.6, 1:41.3, 1:82.5,1:165, 1:2250, from 1:1.9 to 1:15, from 1.1:1 to 1:15, from 1:10.31 to1:165, from 2:1 to 1:2250, or within any range defined between any pairof the foregoing values.

An eighth embodiment includes any composition according to any of thefirst through the seventh embodiments wherein the mixture furthercomprises at least one an agriculturally acceptable agent selected fromthe group consisting of an adjuvant, a carrier, or a safener.

A ninth embodiment includes methods of controlling undesirablevegetation comprising the step of applying or otherwise contactingvegetation and/or soil, and/or water with a herbicidally effectiveamount of at least one mixture according to any of the first through theeighth embodiments.

A tenth embodiment includes methods according to the ninth embodimentwherein undesirable vegetation is controlled according to at leasttechnique selected from the group consisting of: direct-seeded,water-seeded, and/or transplanted rice, cereals, wheat, barley, oats,rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola,sugar beet, soybean, cotton, pineapple, pastures, grasslands,rangelands, fallowland, turf, tree and vine orchards, aquatics,plantation crops, vegetables, industrial vegetation management (IVM), orrights-of-way (ROW).

An eleventh embodiment includes methods according to either of the ninthand tenth embodiments wherein a herbicidally effective amount of themixture is applied either pre- or post-emergently to at least one of thefollowing: a crop, a field, a ROW, or a paddy.

A twelfth embodiment includes methods according to any of the ninththrough the eleventh embodiments wherein the undesirable vegetationcontrolled by an application of a herbicidally effective amount of themixture and at least one of the following phytotoxic actives:glyphosate-, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthaseinhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-,phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transportinhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-,phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-,imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-,triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactatesynthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-,4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-, phytoenedesaturase inhibitor-, carotenoid biosynthesis inhibitor-,protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesisinhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chainfatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-,photosystem I inhibitor-, photosystem II inhibitor-, protoporphyrinogenoxidase (PPO) inhibitor-, triazine-, or bromoxynil-tolerant crops.

A thirteenth embodiment includes a at least one method according to anyof the ninth through the twelfth embodiments wherein a plant that istolerant to at least one herbicide is treated, and where the tolerantcrop possesses multiple or stacked traits conferring tolerance tomultiple herbicides or inhibitors of multiple modes of action, in someembodiments the treated plant that expresses resistance to a herbicideis a itself undesirable vegetation.

A fourteenth embodiment includes methods according to the thirteenthembodiment, wherein the resistant or tolerant weed is a biotype withresistance or tolerance to multiple herbicides, multiple chemicalclasses, inhibitors of multiple herbicide modes-of-action, or viamultiple resistance mechanisms.

A fifteenth embodiment includes at least one of the methods according toeither the thirteenth of fourteenth embodiments, wherein the resistantor tolerant undesirable plant is a biotype resistant or tolerant to atleast on agent selected from the groups consisting of: acetolactatesynthase (ALS) inhibitors or acetohydroxy acid synthase (AHAS),photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors,synthetic auxins, auxin transport inhibitors, photosystem I inhibitors,5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors,microtubule assembly inhibitors, fatty acid and lipid synthesisinhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoidbiosynthesis inhibitors, very long chain fatty acid (VLCFA) inhibitors,phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors,4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors, mitosisinhibitors, cellulose biosynthesis inhibitors, herbicides with multiplemodes-of-action, quinclorac, arylaminopropionic acids, difenzoquat,endothall, or organoarsenicals.

A sixteenth embodiment includes methods of controlling undesirablevegetation comprising the step of applying a herbicidally effectiveamount of at least one mixture according to the fourth embodimentwherein the amount of the mixture is applied at a rate, expressed inai/ha of chlorflurenol-methyl or chlorflurenol selected from the groupof rates and ranges of rates consisting of, about: 68.75, 137.5, 275,550 or within any range defined between any pair of the foregoingvalues.

A seventeenth embodiment includes methods according to either of thefourth and sixteenth embodiments wherein the controlled plant is atleast one plant selected from the group consisting of: ECHCG, ECHCO,CYPIR, LEFCH, IPOHE, DIGSA, ECHOR, SCPMA, still other embodimentsinclude controlling plants from the genera consisting of: Echinochloa,Cyperus, Leptochloa, Ipomoea, Digitaria, Schoenoplectus, andBolboschoenus.

An eighteenth embodiment includes methods of controlling undesirablevegetation comprising the step of applying a herbicidally effectiveamount of at least one a mixture according to the fifth embodimentwherein the amount of the mixture is applied at a rate, expressed inai/ha of diflufenzopyr or diflufenzopyr sodium selected from the groupof rates and ranges of rates consisting of, about: 8.75, 17.5, 35, 70,or within any range defined between any pair of the foregoing values.

A nineteenth embodiment includes methods according to either of thefifth and eighteenth embodiments wherein the controlled plant is atleast one plant selected from the group consisting of: BRAPP, LEFCH,DIGSA, IPOHE, ECHCG, CYPRO, FIMMI, still other embodiments includecontrolling plants from the genera consisting of: Brachiaria,Leptochloa, Digitaria, Ipomoea, Echinochloa, Cyperus, and Fimbristylis.

A twentieth embodiment includes methods of controlling undesirablevegetation comprising the step of applying a herbicidally effectiveamount of at least one a mixture according to the sixth embodimentwherein the amount of the mixture is applied at a rate, expressed inai/ha of flurenol or flurenol-methyl selected from the group of ratesand ranges of rates consisting of, about: 68.75, 137.5, 275, or withinany range defined between any pair of the foregoing values.

A twenty-first embodiment includes methods according to either of thesixth and twentieth embodiments wherein the controlled plant is at leastone plant selected from the group consisting of: BRAPP, CYPIR, ECHCG,FIMMI, CYPRO still other embodiments include controlling plants from thegenera consisting of: Brachiaria, Cyperus, Echinochloa, Fimbristylis,and Cyperus.

A twenty-second embodiment includes methods of controlling undesirablevegetation comprising the step of applying a herbicidally effectiveamount of at least one a mixture according to the seventh embodimentwherein the amount of the mixture is applied at a rate, expressed inai/ha of naptalam selected from the group of rates and ranges of ratesconsisting of, about: 30, 60, 120, 330, 660, 1320, or within any rangedefined between any pair of the foregoing values.

A twenty-third embodiment includes methods according to either of theseventh and twenty-second embodiments wherein the controlled plant is atleast one plant selected from the group consisting of, BRAPP, LEFCH,IPOHE, ECHCG, FIMMI, ECHOR, CYPRO, still other embodiments includecontrolling plants from the genera consisting of: Brachiaria,Leptochloa, Ipomoea, Echinochloa, Fimbristylis, Echinochloa, andCyperus.

Provided herein are herbicidal compositions comprising a herbicidallyeffective amount of (a) a compound of the formula (I)

or an agriculturally acceptable salt or ester of thereof, and (b) anauxin transport inhibitor.

Provided herein are also methods of controlling undesirable vegetationcomprising contacting the vegetation or the locus thereof, i.e., areaadjacent to the vegetation, with or applying to the soil or water toprevent the emergence or growth of vegetation a herbicidally effectiveamount of the compound of formula (I) or agriculturally acceptable saltor ester thereof and (b) an auxin transport inhibitor. In certainembodiments, the methods employ the compositions described herein.

In certain embodiments of the compositions and methods, the auxintransport inhibitor is chlorflurenol-methyl, diflufenzopyr, flurenol andnaptalam, or an agriculturally acceptable salt or ester thereof.

Furthermore, in some embodiments, the combination of compound (I) oragriculturally acceptable salt or ester thereof, and an auxin transportinhibitor, including but not limited to chlorflurenol-methyl,diflufenzopyr, flurenol and naptalam, or an agriculturally acceptablesalt or ester thereof exhibits synergism, e.g., the herbicidal activeingredients are more effective in combination than when appliedindividually. Synergism has been defined as “an interaction of two ormore factors such that the effect when combined is greater than thepredicted effect based on the response of each factor appliedseparately.” Senseman, S., ed. Herbicide Handbook. 9^(th) ed. Lawrence:Weed Science Society of America, 2007. In certain embodiments, thecompositions exhibit synergy as determined by the Colby's equation.Colby, S. R. 1967. Calculation of the synergistic and antagonisticresponse of herbicide combinations. Weeds 15:20-22.

In certain embodiments of the compositions and methods described herein,the compound of formula (I), i.e., the carboxylic acid, is employed. Incertain embodiments, a carboxylate salt of the compound of formula (I)is employed. In certain embodiments, an aralkyl or alkyl ester isemployed. In certain embodiments, a benzyl, substituted benzyl, or C₁₋₄alkyl, e.g., n-butyl ester is employed. In certain embodiments, thebenzyl ester is employed

In some embodiments, the compound of formula (I) or salt or esterthereof and an auxin transport inhibitor, or an agriculturallyacceptable salt or ester thereof, are formulated in one composition,tank mixed, applied simultaneously, or applied sequentially.

Herbicidal activity is exhibited by the compounds when they are applieddirectly to the plant or to the locus of the plant at any stage ofgrowth. The effect observed depends upon the plant species to becontrolled, the stage of growth of the plant, the application parametersof dilution and spray drop size, the particle size of solid components,the environmental conditions at the time of use, the specific compoundemployed, the specific adjuvants and carriers employed, the soil type,and the like, as well as the amount of chemical applied. These and otherfactors can be adjusted to promote non-selective or selective herbicidalaction. In some embodiments, the compositions described herein areapplied as a post-emergence application, pre-emergence application, orin-water application to flooded paddy rice or water bodies (e.g., ponds,lakes and streams), to relatively immature undesirable vegetation toachieve the maximum control of weeds.

In some embodiments, the compositions and methods provided herein areutilized to control weeds in crops, including but not limited todirect-seeded rice, water-seeded rice, transplanted rice, cereals,wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower,oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures,grasslands, rangelands, fallowland, turf, tree and vine orchards,aquatics, plantation crops, vegetables, industrial vegetation management(IVM) and rights-of-way (ROW).

In certain embodiments, the compositions and methods provided herein areutilized to control weeds in rice. In certain embodiments, the rice isdirect-seeded, water-seeded, or transplanted rice.

The compositions and methods described herein may be used to controlundesirable vegetation on glyphosate-tolerant-,5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-tolerant-,glufosinate-tolerant-, glutamine synthetase inhibitor-tolerant-,dicamba-tolerant-, phenoxy auxin-tolerant-, pyridyloxy auxin-tolerant-,auxin-tolerant-, auxin transport inhibitor-tolerant-,aryloxyphenoxypropionate-tolerant-, cyclohexanedione-tolerant-,phenylpyrazoline-tolerant-, acetyl CoA carboxylase (ACCase)inhibitor-tolerant-, imidazolinone-tolerant-, sulfonylurea-tolerant-,pyrimidinylthiobenzoate-tolerant-, triazolopyrimidine-tolerant-,sulfonylaminocarbonyltriazolinone-tolerant-, acetolactate synthase (ALS)or acetohydroxy acid synthase (AHAS) inhibitor-tolerant-,4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-tolerant-,phytoene desaturase inhibitor-tolerant-, carotenoid biosynthesisinhibitor-tolerant-, protoporphyrinogen oxidase (PPO)inhibitor-tolerant-, cellulose biosynthesis inhibitor-tolerant-, mitosisinhibitor-tolerant-, microtubule inhibitor-tolerant-, very long chainfatty acid inhibitor-tolerant-, fatty acid and lipid biosynthesisinhibitor-tolerant-, photosystem I inhibitor-tolerant-, photosystem IIinhibitor-tolerant-, triazine-tolerant-, and bromoxynil-tolerant-crops(such as, but not limited to, soybean, cotton, canola/oilseed rape,rice, cereals, corn, sorghum, sunflower, sugar beet, sugarcane, turf,etc.), for example, in conjunction with glyphosate, EPSP synthaseinhibitors, glufosinate, glutamine synthase inhibitors, dicamba, phenoxyauxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors,aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, ACCaseinhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates,triazolopyrimidines, sulfonylaminocarbonyltriazolinones, ALS or AHASinhibitors, HPPD inhibitors, phytoene desaturase inhibitors, carotenoidbiosynthesis inhibitors, PPO inhibitors, cellulose biosynthesisinhibitors, mitosis inhibitors, microtubule inhibitors, very long chainfatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors,photosystem I inhibitors, photosystem II inhibitors, triazines, andbromoxynil. The compositions and methods may be used in controllingundesirable vegetation in crops possessing multiple or stacked traitsconferring tolerance to multiple chemistries and/or inhibitors ofmultiple modes of action. In some embodiments, the compound of formula(I) or salt or ester thereof and complementary herbicide or salt orester thereof are used in combination with herbicides that are selectivefor the crop being treated and which complement the spectrum of weedscontrolled by these compounds at the application rate employed. In someembodiments, the compositions described herein and other complementaryherbicides are applied at the same time, either as a combinationformulation or as a tank mix, or sequentially.

The compositions and methods may be used in controlling undesirablevegetation in crops possessing agronomic stress tolerance (including butnot limited to drought, cold, heat, salt, water, nutrient, fertility,pH), pest tolerance (including but not limited to insects, fungi andpathogens) and crop improvement traits (including but not limited toyield; protein, carbohydrate, or oil content; protein, carbohydrate, oroil composition; plant stature and plant architecture).

The compositions and methods provided herein are utilized to controlundesirable vegetation. Undesirable vegetation includes, but is notlimited to, undesirable vegetation that occurs in rice, cereals, wheat,barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseedrape, canola, sugar beet, soybean, cotton, pineapple, pastures,grasslands, rangelands, fallowland, turf, tree and vine orchards,aquatics, plantation crops, vegetables, industrial vegetation management(IVM) and rights-of-way (ROW).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation in rice. In certain embodiments, the undesirablevegetation is Brachiaria platyphylla (Groseb.) Nash or Urochloaplatyphylla (Nash) R. D. Webster (broadleaf signalgrass, BRAPP),Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloaspecies (ECHSS), Echinochloa crus-galli (L.) P. Beauv. (barnyardgrass,ECHCG), Echinochloa crus-pavonis (Kunth) Schult. (gulf cockspur, ECHCV),Echinochloa colonum (L.) LINK (junglerice, ECHCO), Echinochloa oryzoides(Ard.) Fritsch (early watergrass, ECHOR), Echinochloa oryzicola(Vasinger) Vasinger (late watergrass, ECHPH), Echinochloa phyllopogon(Stapf) Koso-Pol. (rice barnyardgrass, ECHPH), Echinochloa polystachya(Kunth) Hitchc. (creeping river grass, ECHPO), Ischaemum rugosum Salisb.(saramollagrass, ISCRU), Leptochloa chinensis (L.) Nees (Chinesesprangletop, LEFCH), Leptochloa fascicularis (Lam.) Gray (beardedsprangletop, LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazonsprangletop, LEFPA), Oryza species (red and weedy rice, ORYSS), Panicumdichotomiflorum (L.) Michx. (fall panicum, PANDI), Paspalum dilatatumPoir. (dallisgrass, PASDI), Rottboellia cochinchinensis (Lour.) W. D.Clayton (itchgrass, ROOEX), Cyperus species (CYPSS), Cyperus difformisL. (smallflower flatsedge, CYPDI), Cyperus dubius Rottb. (MAPDU),Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus iria L. (riceflatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Cyperusserotinus Rottb./C. B. Clarke (tidalmarsh flatsedge, CYPSE), Eleocharisspecies (ELOSS), Fimbristylis miliacea (L.) Vahl (globe fringerush,FIMMI), Schoenoplectus species (SCPSS), Schoenoplectus juncoides Roxb.(Japanese bulrush, SCPJU), Bolboschoenus maritimus (L.) Palla orSchoenoplectus maritimus L. Lye (sea clubrush, SCPMA), Schoenoplectusmucronatus L. (ricefield bulrush, SCPMU), Aeschynomene species,(jointvetch, AESSS), Alternanthera philoxeroides (Mart.) Griseb.(alligatorweed, ALRPH), Alisma plantago-aquatica L. (commonwaterplantain, ALSPA), Amaranthus species, (pigweeds and amaranths,AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Commelinabenghalensis L. (Benghal dayflower, COMBE), Eclipta alba (L.) Hassk.(American false daisy, ECLAL), Heteranthera limosa (SW.) Willd./Vahl(ducksalad, HETLI), Heteranthera reniformis R. & P. (roundleafmudplantain, HETRE), Ipomoea species (morningglories, IPOSS), Ipomoeahederacea (L.) Jacq. (ivyleaf morningglory, IPOHE), Lindernia dubia (L.)Pennell (low false pimpernel, LIDDU), Ludwigia species (LUDSS), Ludwigialinifolia Poir. (southeastern primrose-willow, LUDLI), Ludwigiaoctovalvis (Jacq.) Raven (longfruited primrose-willow, LUDOC),Monochoria korsakowii Regel & Maack (monochoria, MOOKA), Monochoriavaginalis (Burm. F.) C. Presl ex Kuhth, (monochoria, MOOVA), Murdannianudiflora (L.) Brenan (doveweed, MUDNU), Polygonum pensylvanicum L.,(Pennsylvania smartweed, POLPY), Polygonum persicaria L. (ladysthumb,POLPE), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Rotalaindica (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species,(arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (hempsesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation in cereals. In certain embodiments, theundesirable vegetation is Alopecurus myosuroides Huds. (blackgrass,ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L.(wild oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), Loliummultiflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz.(littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POANN),Setaria pumila (Poir.) Roemer & J. A. Schultes (yellow foxtail, SETLU),Setaria viridis (L.) Beauv. (green foxtail, SETVI), Amaranthusretroflexus L. (redroot pigweed, AMARE), Brassica species (BRSSS),Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.)Scop. (Canada thistle, CIRAR), Galium aparine L. (catchweed bedstraw,GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium purpureumL. (purple deadnettle, LAMPU), Matricaria recutita L. (wild chamomile,MATCH), Matricaria matricarioides (Less.) Porter (pineappleweed, MATMT),Papaver rhoeas L. (common poppy, PAPRH), Polygonuum convolvulus L. (wildbuckwheat, POLCO), Salsola tragus L. (Russian thistle, SASKR), Sinapisspecies (SINSS), Sinapis arvensis L. (wild mustard, SINAR), Stellariamedia (L.) Vill. (common chickweed, STEME), Veronica persica Poir.(Persian speedwell, VERPE), Viola arvensis Murr. (field violet, VIOAR),or Viola tricolor L. (wild violet, VIOTR).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation in range and pasture, fallowland, IVM and ROW. Incertain embodiments, the undesirable vegetation is Ambrosiaartemisiifolia L. (common ragweed, AMBEL), Cassia obtusifolia (sicklepod, CASOB), Centaurea maculosa auct. non Lam. (spotted knapweed,CENMA), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Convolvulusarvensis L. (field bindweed, CONAR), Daucus carota L. (wild carrot,DAUCA), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriolaL./Torn. (prickly lettuce, LACSE), Plantago lanceolata L. (buckhornplantain, PLALA), Rumex obtusifolius L. (broadleaf dock, RUMOB), Sidaspinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard,SINAR), Sonchus arvensis L. (perennial sowthistle, SONAR), Solidagospecies (goldenrod, SOOSS), Taraxacum officinale G. H. Weber ex Wiggers(dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urticadioica L. (common nettle, URTDI).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation found in row crops, tree and vine crops, andperennial crops. In certain embodiments, the undesirable vegetation isAlopecurus myosuroides Huds. (blackgrass, ALOMY), Avena fatua L. (wildoat, AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf)R. D. Webster (Surinam grass, BRADC), Brachiaria brizantha (Hochst. exA. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) R.D. (beardgrass, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloaplatyphylla (Nash) R. D. Webster (broadleaf signalgrass, BRAPP),Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea (Link) R.D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L. (southernsandbar, CENEC), Digitaria horizontalis Willd. (Jamaican crabgrass,DIGHO), Digitaria insularis (L.) Mez ex Ekman (sourgrass, TRCIN),Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloacrus-galli (L.) P. Beauv. (barnyardgrass, ECHCG), Echinochloa colonum(L.) Link (junglerice, ECHCO), Eleusine indica (L.) Gaertn. (goosegrass,ELEIN), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Panicumdichotomiflorum Michx. (fall panicum, PANDI), Panicum miliaceum L.(wild-proso millet, PANMI), Setaria faberi Herrm. (giant foxtail,SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghumhalepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.) Moenchssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellownutsedge, CYPES), Cyperus rotundus L. (purple nutsedge, CYPRO), Abutilontheophrasti Medik. (velvetleaf, ABUTH), Amaranthus species (pigweeds andamaranths, AMASS), Ambrosia artemisiifolia L. (common ragweed, AMBEL),Ambrosia psilostachya DC. (western ragweed, AMBPS), Ambrosia trifida L.(giant ragweed, AMBTR), Anoda cristata (L.) Schlecht. (spurred anoda,ANVCR), Asclepias syriaca L. (common milkweed, ASCSY), Bidens pilosa L.(hairy beggarticks, BIDPI), Borreria species (BOISS), Borreria alata(Aubl.) DC. or Spermacoce alata Aubl. (broadleaf buttonweed, BOILF),Spermacose latifolia (broadleaved button weed, BOILF), Chenopodium albumL. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canadathistle, CIRAR), Commelina benghalensis L. (tropical spiderwort, COMBE),Datura stramonium L. (jimsonweed, DATST), Daucus carota L. (wild carrot,DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL), Euphorbiahirta L. or Chamaesyce hirta (L.) Millsp. (garden spurge, EPHHI),Euphorbia dentata Michx. (toothed spurge, EPHDE), Erigeron bonariensisL. or Conyza bonariensis (L.) Cronq. (hairy fleabane, ERIBO), Erigeroncanadensis L. or Conyza canadensis (L.) Cronq. (Canadian fleabane,ERICA), Conyza sumatrensis (Retz.) E. H. Walker (tall fleabane, ERIFL),Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia(L.) Griseb. (smallflower morningglory, IAQTA), Ipomoea hederacea (L.)Jacq. (ivyleaf morningglory, IPOHE), Ipomoea lacunosa L. (whitemorningglory, IPOLA), Lactuca serriola L./Torn. (prickly lettuce,LACSE), Portulaca oleracea L. (common purslane, POROL), Richardiaspecies (pusley, RCHSS), Sida species (sida, SIDSS), Sida spinosa L.(prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR),Solanum ptychanthum Dunal (eastern black nightshade, SOLPT), Tridaxprocumbens L. (coat buttons, TRQPR), or Xanthium strumarium L. (commoncocklebur, XANST).

In some embodiments, the methods provided herein are utilized to controlundesirable vegetation in turf. In certain embodiments, the undesirablevegetation is Bellis perennis L. (English daisy, BELPE), Cyperusesculentus L. (yellow nutsedge, CYPES), Cyperus species (CYPSS),Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Diodiavirginiana L. (Virginia buttonweed, DIQVI), Euphorbia species (spurges,EPHSS), Glechoma hederacea L. (ground ivy, GLEHE), Hydrocotyle umbellataL. (dollarweed, HYDUM), Kyllinga species (kyllinga, KYLSS), Lamiumamplexicaule L. (henbit, LAMAM), Murdannia nudiflora (L.) Brenan(doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago major L.(broadleaf plantain, PLAMA), Plantago lanceolata L. (buckhorn/narrowleafplantain, PLALA), Phyllanthus urinaria L. (chamberbitter, PYLTE), Rumexobtusifolius L. (broadleaf dock, RUMOB), Stachys floridana Shuttlew.(Florida betony, STAFL), Stellaria media (L.) Vill. (common chickweed,STEME), Taraxacum officinale G. H. Weber ex Wiggers (dandelion, TAROF),Trifolium repens L. (white clover, TRFRE), or Viola species (wildviolet, VIOSS).

In some embodiments, the compositions and methods provided herein areutilized to control undesirable vegetation consisting of grass,broadleaf and sedge weeds. In certain embodiments, the compositions andmethods provided herein are utilized to control undesirable vegetationincluding Brachiaria or Urochloa, Cyperus, Digitaria, Echinochloa,Fimbristylis, Ipomoea, Leptochloa and Schoenoplectus/Bolboschoenus.

In some embodiments, the combination of compound (I) or agriculturallyacceptable ester or salt thereof and chlorflurenol, diflufenzopyr,flurenol and naptalam, or agriculturally acceptable salt or esterthereof is used to control Brachiaria platyphylla (Griseb.) Nash orUrochloa platyphylla (Nash) R. D. Webster (broadleaf signalgrass,BRAPP), Cyperus iria L. (rice flatsedge, CYPIR), Cyperus rotundus L.(purple nutsedge, CYPRO), Digitaria sanguinalis (L.) Scop. (largecrabgrass, DIGSA), Echinochloa crus-galli (L.) Beauv. (barnyardgrass,ECHCG), Echinochloa colona (L.) Link (junglerice, ECHCO), Echinochloaoryzoides (Ard.) Fritsch (early watergrass, ECHOR), Fimbristylismiliacea (L.) Vahl (globe fringerush, FIMMI), Ipomoea hederacea Jacq.(ivyleaf morningglory, IPOHE), Leptochloa chinensis (L.) Nees (Chinesesprangletop, LEFCH) and Schoenoplectus maritimus (L.) Lye orBolboschoenus maritimus (L.) Palla (sea clubrush, SCPMA).

The compounds of formula I or agriculturally acceptable salt or esterthereof may be used to control herbicide resistant or tolerant weeds.The methods employing the combination of a compound of formula I oragriculturally acceptable salt or ester thereof and the compositionsdescribed herein may also be employed to control herbicide resistant ortolerant weeds. Exemplary resistant or tolerant weeds include, but arenot limited to, biotypes resistant or tolerant to acetolactate synthase(ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g.,imidazolinones, sulfonylureas, pyrimidinylthiobenzoates,triazolopyrimidines, sulfonylaminocarbonyltriazolinones), photosystem IIinhibitors (e.g., phenylcarbamates, pyridazinones, triazines,triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles,phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (e.g.,aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines),synthetic auxins (e.g., benzoic acids, phenoxycarboxylic acids, pyridinecarboxylic acids, quinoline carboxylic acids), auxin transportinhibitors (e.g., phthalamates, semicarbazones), photosystem Iinhibitors (e.g., bipyridyliums), 5-enolpyruvylshikimate-3-phosphate(EPSP) synthase inhibitors (e.g., glyphosate), glutamine synthetaseinhibitors (e.g., glufosinate, bialafos), microtubule assemblyinhibitors (e.g., benzamides, benzoic acids, dinitroanilines,phosphoramidates, pyridines), mitosis inhibitors (e.g., carbamates),very long chain fatty acid (VLCFA) inhibitors (e.g., acetamides,chloroacetamides, oxyacetamides, tetrazolinones), fatty acid and lipidbiosynthesis inhibitors (e.g., phosphorodithioates, thiocarbamates,benzofuranes, chlorocarbonic acids), protoporphyrinogen oxidase (PPO)inhibitors (e.g., diphenylethers, N-phenylphthalimides, oxadiazoles,oxazolidinediones, phenylpyrazoles, pyrimidindiones, thiadiazoles,triazolinones), carotenoid biosynthesis inhibitors (e.g., clomazone,amitrole, aclonifen), phytoene desaturase (PDS) inhibitors (e.g.,amides, anilidex, furanones, phenoxybutan-amides, pyridiazinones,pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors(e.g., callistemones, isoxazoles, pyrazoles, triketones), cellulosebiosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac,triazolocarboxamides), herbicides with multiple modes-of-action such asquinclorac, and unclassified herbicides such as arylaminopropionicacids, difenzoquat, endothall, and organoarsenicals. Exemplary resistantor tolerant weeds include, but are not limited to, biotypes withresistance or tolerance to multiple herbicides, biotypes with resistanceor tolerance to multiple chemical classes, biotypes with resistance ortolerance to multiple herbicide modes-of-action, and biotypes withmultiple resistance or tolerance mechanisms (e.g., target siteresistance or metabolic resistance).

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with chlorflurenol-methyl or carboxylic acid or carboxylatesalt thereof or other ester. With regard to the compositions, in someembodiments, the weight ratio of the compound of formula (I) or salt orester thereof to chlorflurenol-methyl or carboxylic acid or carboxylatesalt thereof or other ester is within the range from about 1:1680 toabout 4.4:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to chlorflurenol-methyl orcarboxylic acid or carboxylate salt thereof or other ester is within therange from 1:63 to about 1:4. In certain embodiments, the weight ratioof the compound of formula (I) or salt or ester thereof tochlorflurenol-methyl or carboxylic acid or carboxylate salt thereof orother ester is within the range from about 1:250 to about 1:4. Incertain embodiments, the weight ratio of the compound of formula (I) orsalt or ester thereof to chlorflurenol-methyl or carboxylic acid orcarboxylate salt thereof or other ester is within the range from about1:125 to about 1:7.8. In certain embodiments, the compositions providedherein comprise the compound of formula (I) or its benzyl ester andchlorflurenol-methyl or carboxylic acid or carboxylate salt thereof orother ester. In one embodiment, the composition comprises the compoundof formula (I) and chlorflurenol-methyl or carboxylic acid orcarboxylate salt thereof or other ester, wherein the weight ratio of thecompound of formula (I) to chlorflurenol-methyl or carboxylic acid orcarboxylate salt thereof or other ester is about 1:63 to about 1:7.8. Inone embodiment, the composition comprises the benzyl ester of thecompound of formula (I) and chlorflurenol-methyl or carboxylic acid orcarboxylate salt thereof or other ester, wherein the weight ratio of thebenzyl ester of the compound of formula (I) to chlorflurenol-methyl orcarboxylic acid or carboxylate salt thereof or other ester is about1:125 to about 1:7.8. With respect to the methods, in certainembodiments, the methods comprise contacting the undesirable vegetationor locus thereof or applying to the soil or water to prevent theemergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate fromabout 70 grams active ingredient per hectare (gai/ha) to about 3360gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate from about 72 grams active ingredient per hectare(gai/ha) to about 300 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andchlorflurenol-methyl or carboxylic acid or carboxylate salt thereof orother ester, e.g., sequentially or simultaneously. In some embodiments,the chlorflurenol-methyl or carboxylic acid or carboxylate salt thereofor other esteris applied at a rate from about 280 gai/ha to about 3360gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, the chlorflurenol-methyl or carboxylic acid or carboxylatesalt thereof or other ester is applied at a rate from about 35 gai/ha toabout 1100 gai/ha and the compound of formula (I) of salt or esterthereof is applied at a rate from about 2 g acid equivalent per hectare(gae/ha) to about 70 gae/ha. In some embodiments, thechlorflurenol-methyl or carboxylic acid or carboxylate salt thereof orother ester is applied at a rate from about 68.75 gai/ha to about 550gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 4.38 g acid equivalent per hectare (gae/ha)to about 35 gae/ha. In certain embodiments, the methods utilize thecompound of formula (I), or its benzyl ester and chlorflurenol-methyl orcarboxylic acid or carboxylate salt thereof or other ester. In oneembodiment, the methods utilize the compound of formula (I) andchlorflurenol-methyl or carboxylic acid or carboxylate salt thereof orother ester, wherein the compound of formula (I) is applied at a ratefrom about 4.38 g acid equivalent per hectare (gae/ha) to about 35gae/ha, and chlorflurenol-methyl or carboxylic acid or carboxylate saltthereof or other ester is applied at a rate of about 68.8 gai/ha toabout 550 gai/ha. In one embodiment, the methods utilize the benzylester of the compound of formula (I) and chlorflurenol-methyl orcarboxylic acid or carboxylate salt thereof or other ester, wherein thebenzyl ester of the compound of formula (I) is applied at a rate fromabout 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha,and chlorflurenol-methyl or carboxylic acid or carboxylate salt thereofor other ester is applied at a rate of about 68.75 gai/ha to about 550gai/ha. In certain embodiments, the methods and compositions utilizingthe compound of formula (I) or salt or ester thereof in combination withchlorflurenol-methyl or carboxylic acid or carboxylate salt thereof orother ester are used to control ECCHG, ECHCO, CYPIR, LEFCH, IPOHE,DIGSA, ECHOR, or SCPMA.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with diflufenzopyr, diflufenzopyr sodium, or salt,carboxylic acid, carboxylate salt, or ester thereof. With regard to thecompositions, in some embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to diflufenzopyr, diflufenzopyrsodium, salt, carboxylic acid, carboxylate salt, or ester thereof iswithin the range from about 1:18 to about 86:1. In certain embodiments,the weight ratio of the compound of formula (I) or salt or ester thereofto diflufenzopyr, diflufenzopyr sodium or salt, carboxylic acid,carboxylate salt, or ester thereof is within the range from 1:8 to about2:1. In certain embodiments, the weight ratio of the compound of formula(I) or salt or ester thereof to diflufenzopyr or salt, carboxylic acid,carboxylate salt, or ester thereof is within the range from about 1:14to about 4:1. In certain embodiments, the weight ratio of the compoundof formula (I) or salt or ester thereof to diflufenzopyr or salt,carboxylic acid, carboxylate salt, or ester thereof is within the rangefrom about 1:7 to about 2:1. In certain embodiments, the compositionsprovided herein comprise the compound of formula (I) or its benzyl esterand diflufenzopyr or salt, carboxylic acid, carboxylate salt, or esterthereof. In one embodiment, the composition comprises the compound offormula (I) and diflufenzopyr or salt, carboxylic acid, carboxylatesalt, or ester thereof, wherein the weight ratio of the compound offormula (I) to diflufenzopyr or salt, carboxylic acid, carboxylate salt,or ester thereof is about 1:7 to about 2:1. In one embodiment, thecomposition comprises the benzyl ester of the compound of formula (I)and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or esterthereof, wherein the weight ratio of the benzyl ester of the compound offormula (I) to diflufenzopyr or salt, carboxylic acid, carboxylate salt,or ester thereof is about 1:4 to about 2:1. With respect to the methods,in certain embodiments, the methods comprise contacting the undesirablevegetation or locus thereof or applying to the soil or water to preventthe emergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate fromabout 5 grams active ingredient per hectare (gai/ha) to about 335 gai/habased on the total amount of active ingredients in the composition. Incertain embodiments, the composition is applied at an application ratefrom about 12 grams active ingredient per hectare (gai/ha) to about 60gai/ha based on the total amount of active ingredients in thecomposition. In some embodiments, the methods comprise contacting theundesirable vegetation or locus thereof or applying to the soil or waterto prevent the emergence or growth of vegetation with a compound offormula (I) or salt or ester thereof and diflufenzopyr or salt,carboxylic acid, carboxylate salt, or ester thereof, e.g., sequentiallyor simultaneously. In some embodiments, the diflufenzopyr or salt orester thereof is applied at a rate from about 3.5 gai/ha to about 35gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In someembodiments, the diflufenzopyr or salt, carboxylic acid, carboxylatesalt, or ester thereof is applied at a rate from about 4 gai/ha to about70 gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 g acid equivalent per hectare (gae/ha) toabout 35 gae/ha. In some embodiments, the diflufenzopyr or salt,carboxylic acid, carboxylate salt, or ester thereof is applied at a ratefrom about 8.75 gai/ha to about 35 gai/ha and the compound of formula(I) of salt or ester thereof is applied at a rate from about 4.38 g acidequivalent per hectare (gae/ha) to about 17.5 gae/ha. In certainembodiments, the methods utilize the compound of formula (I), or itsbenzyl ester and diflufenzopyr or salt, carboxylic acid, carboxylatesalt, or ester thereof. In one embodiment, the methods utilize thecompound of formula (I) and diflufenzopyr or salt, carboxylic acid,carboxylate salt, or ester thereof, wherein the compound of formula (I)is applied at a rate from about 4.38 g acid equivalent per hectare(gae/ha) to about 17.5 gae/ha, and diflufenzopyr or salt, carboxylicacid, carboxylate salt, or ester thereof is applied at a rate of about8.75 gai/ha to about 35 gai/ha. In one embodiment, the methods utilizethe benzyl ester of the compound of formula (I) and diflufenzopyr orsalt, carboxylic acid, carboxylate salt, or ester thereof, wherein thebenzyl ester of the compound of formula (I) is applied at a rate fromabout 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha,and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or esterthereof is applied at a rate of about 8.75 gai/ha to about 35 gai/ha. Incertain embodiments, the methods and compositions utilizing the compoundof formula (I) or salt or ester thereof in combination withdiflufenzopyr, diflufenzopyr sodium, or salt, carboxylic acid,carboxylate salt, or ester thereof or salt or ester thereof are used tocontrol BRAPP, CYPRO, ECHCG, ECHCO, LEFCH, DIGSA, or IPOHE.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with diflufenzopyr, diflufenzopyr sodium, or salt,carboxylic acid, carboxylate salt, or ester thereof. With regard to thecompositions, in some embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to diflufenzopyr, diflufenzopyrsodium, salt, carboxylic acid, carboxylate salt, or ester thereof iswithin the range from about 1:18 to about 86:1. In certain embodiments,the weight ratio of the compound of formula (I) or salt or ester thereofto diflufenzopyr, diflufenzopyr sodium or salt, carboxylic acid,carboxylate salt, or ester thereof is within the range from 1:8 to about2:1. In certain embodiments, the weight ratio of the compound of formula(I) or salt or ester thereof to diflufenzopyr or salt, carboxylic acid,carboxylate salt, or ester thereof is within the range from about 1:14to about 4:1. In certain embodiments, the weight ratio of the compoundof formula (I) or salt or ester thereof to diflufenzopyr or salt,carboxylic acid, carboxylate salt, or ester thereof is within the rangefrom about 1:7 to about 2:1. In certain embodiments, the compositionsprovided herein comprise the compound of formula (I) or its benzyl esterand diflufenzopyr or salt, carboxylic acid, carboxylate salt, or esterthereof. In one embodiment, the composition comprises the compound offormula (I) and diflufenzopyr or salt, carboxylic acid, carboxylatesalt, or ester thereof, wherein the weight ratio of the compound offormula (I) to diflufenzopyr or salt, carboxylic acid, carboxylate salt,or ester thereof is about 1:7 to about 2:1. In one embodiment, thecomposition comprises the benzyl ester of the compound of formula (I)and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or esterthereof, wherein the weight ratio of the benzyl ester of the compound offormula (I) to diflufenzopyr or salt, carboxylic acid, carboxylate salt,or ester thereof is about 1:4 to about 2:1. In one embodiment, thecomposition comprises the benzyl ester of the compound of formula (I)and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or esterthereof, wherein the weight ratio of the benzyl ester of the compound offormula (I) to diflufenzopyr or salt, carboxylic acid, carboxylate salt,or ester thereof is about 1:16 to about 4:1. With respect to themethods, in certain embodiments, the methods comprise contacting theundesirable vegetation or locus thereof or applying to the soil or waterto prevent the emergence or growth of vegetation a composition describedherein. In some embodiments, the composition is applied at anapplication rate from about 5 grams active ingredient per hectare(gai/ha) to about 335 gai/ha based on the total amount of activeingredients in the composition. In certain embodiments, the compositionis applied at an application rate from about 12 grams active ingredientper hectare (gai/ha) to about 60 gai/ha based on the total amount ofactive ingredients in the composition. In certain embodiments, thecomposition is applied at an application rate from about 12 grams activeingredient per hectare (gai/ha) to about 102 gai/ha based on the totalamount of active ingredients in the composition. In some embodiments,the methods comprise contacting the undesirable vegetation or locusthereof or applying to the soil or water to prevent the emergence orgrowth of vegetation with a compound of formula (I) or salt or esterthereof and diflufenzopyr or salt, carboxylic acid, carboxylate salt, orester thereof, e.g., sequentially or simultaneously. In someembodiments, the diflufenzopyr or salt or ester thereof is applied at arate from about 3.5 gai/ha to about 35 gai/ha and the compound offormula (I) of salt or ester thereof is applied at a rate from about 2gae/ha to about 300 gae/ha. In some embodiments, the diflufenzopyr orsalt, carboxylic acid, carboxylate salt, or ester thereof is applied ata rate from about 4 gai/ha to about 70 gai/ha and the compound offormula (I) of salt or ester thereof is applied at a rate from about 2 gacid equivalent per hectare (gae/ha) to about 35 gae/ha. In someembodiments, the diflufenzopyr or salt, carboxylic acid, carboxylatesalt, or ester thereof is applied at a rate from about 8.75 gai/ha toabout 35 gai/ha and the compound of formula (I) of salt or ester thereofis applied at a rate from about 4.38 g acid equivalent per hectare(gae/ha) to about 17.5 gae/ha. In some embodiments, the diflufenzopyr orsalt, carboxylic acid, carboxylate salt, or ester thereof is applied ata rate from about 8.75 gai/ha to about 70 gai/ha and the compound offormula (I) of salt or ester thereof is applied at a rate from about4.38 g acid equivalent per hectare (gae/ha) to about 32 gae/ha. Incertain embodiments, the methods utilize the compound of formula (I), orits benzyl ester and diflufenzopyr or salt, carboxylic acid, carboxylatesalt, or ester thereof. In one embodiment, the methods utilize thecompound of formula (I) and diflufenzopyr or salt, carboxylic acid,carboxylate salt, or ester thereof, wherein the compound of formula (I)is applied at a rate from about 4.38 g acid equivalent per hectare(gae/ha) to about 17.5 gae/ha, and diflufenzopyr or salt, carboxylicacid, carboxylate salt, or ester thereof is applied at a rate of about8.75 gai/ha to about 35 gai/ha. In one embodiment, the methods utilizethe compound of formula (I) and diflufenzopyr or salt, carboxylic acid,carboxylate salt, or ester thereof, wherein the compound of formula (I)is applied at a rate from about 4.38 g acid equivalent per hectare(gae/ha) to about 32 gae/ha, and diflufenzopyr or salt, carboxylic acid,carboxylate salt, or ester thereof is applied at a rate of about 8.75gai/ha to about 70 gai/ha. In one embodiment, the methods utilize thebenzyl ester of the compound of formula (I) and diflufenzopyr or salt,carboxylic acid, carboxylate salt, or ester thereof, wherein the benzylester of the compound of formula (I) is applied at a rate from about4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, anddiflufenzopyr or salt, carboxylic acid, carboxylate salt, or esterthereof is applied at a rate of about 8.75 gai/ha to about 35 gai/ha. Incertain embodiments, the methods and compositions utilizing the compoundof formula (I) or salt or ester thereof in combination withdiflufenzopyr, diflufenzopyr sodium, or salt, carboxylic acid,carboxylate salt, or ester thereof or salt or ester thereof are used tocontrol BRAPP, CYPRO, ECHCG, ECHCO, LEFCH, DIGSA, or IPOHE.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination flurenol, flurenol-methyl or carboxylate salt or esterthereof. With regard to the compositions, in some embodiments, theweight ratio of the compound of formula (I) or salt or ester thereof toflurenol or carboxylate salt or ester thereof is within the range fromabout 1:1680 to about 4.4:1. In certain embodiments, the weight ratio ofthe compound of formula (I) or salt or ester thereof to flurenol orcarboxylate salt or ester thereof is within the range from 1:63 to about1:4. In certain embodiments, the compositions comprise the compound offormula (I) or its benzyl or n-butyl ester and flurenol or carboxylatesalt or ester thereof. With respect to the methods, in certainembodiments, the methods comprise contacting the undesirable vegetationor locus thereof or applying to the soil or water to prevent theemergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate fromabout 70 grams active ingredient per hectare (gai/ha) to about 3360gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate from about 72 grams active ingredient per hectare(gai/ha) to about 300 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andflurenol or carboxylate salt or ester thereof, e.g., sequentially orsimultaneously. In some embodiments, the flurenol or carboxylate salt orester thereof is applied at a rate from about 280 gai/ha to about 3360gai/ha and the compound of formula (I) of salt or ester thereof isapplied at a rate from about 2 gae/ha to about 300 gae/ha. In certainembodiments, the methods utilize the compound of formula (I) or itsbenzyl or n-butyl ester and flurenol or carboxylate salt or esterthereof are used to control BRAPP, ECHCG, CYPIR, CYPRO, or FIMMI.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with naptalam or salt or carboxylate salt or ester thereof.With regard to the compositions, in some embodiments, the weight ratioof the compound of formula (I) or salt or ester thereof to naptalam orsalt or carboxylate salt or ester thereof is within the range from about1:2250 to about 4.2:1. In certain embodiments, the weight ratio of thecompound of formula (I) or salt or ester thereof to naptalam or salt orcarboxylate salt or ester thereof is within the range from 1:250 toabout 1:2. In certain embodiments, the compositions comprise thecompound of formula (I) or its benzyl or n-butyl ester and naptalam orsalt or carboxylate salt or ester thereof. With respect to the methods,in certain embodiments, the methods comprise contacting the undesirablevegetation or locus thereof or applying to the soil or water to preventthe emergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate fromabout 142 grams active ingredient per hectare (gai/ha) to about 4,800gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate from about 145 grams acid equivalent per hectare(gai/ha) to about 1,170 gai/ha based on the total amount of activeingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andnaptalam or salt or carboxylate salt or ester thereof, e.g.,sequentially or simultaneously. In some embodiments, the naptalam orsalt or carboxylate salt or ester thereof is applied at a rate fromabout 140 gai/ha to about 4,500 gai/ha and the compound of formula (I)of salt or ester thereof is applied at a rate from about 2 gae/ha toabout 300 gae/ha. In certain embodiments, the methods utilize thecompound of formula (I) or its benzyl or n-butyl ester and naptalam orsalt or carboxylate salt or ester thereof are used to control BRAPP,CYPRO, ECHCG ECHOR or FIMMI.

In certain embodiments of the compositions and methods described herein,the compound of formula (I) or salt or ester thereof is used incombination with naptalam or salt or carboxylate salt or ester thereof.With regard to the compositions, in some embodiments, the weight ratioof the compound of formula (I) or salt or ester thereof to naptalam orsalt or carboxylate salt or ester thereof is within the range from about1:2250 to about 4.2:1. In certain embodiments, the weight ratio of thecompound of formula (I) or salt or ester thereof to naptalam or salt orcarboxylate salt or ester thereof is within the range from 1:165 toabout 1:1. In certain embodiments, the weight ratio of the compound offormula (I) or salt or ester thereof to naptalam or salt or carboxylatesalt or ester thereof is within the range from 1:250 to about 1:2. Incertain embodiments, the compositions comprise the compound of formula(I) or its benzyl or n-butyl ester and naptalam or salt or carboxylatesalt or ester thereof. With respect to the methods, in certainembodiments, the methods comprise contacting the undesirable vegetationor locus thereof or applying to the soil or water to prevent theemergence or growth of vegetation a composition described herein. Insome embodiments, the composition is applied at an application rate fromabout 142 grams active ingredient per hectare (gai/ha) to about 4,800gai/ha based on the total amount of active ingredients in thecomposition. In certain embodiments, the composition is applied at anapplication rate from about 145 grams acid equivalent per hectare(gai/ha) to about 1,170 gai/ha based on the total amount of activeingredients in the composition. In certain embodiments, the compositionis applied at an application rate from about 38 grams acid equivalentper hectare (gai/ha) to about 1,352 gai/ha based on the total amount ofactive ingredients in the composition. In some embodiments, the methodscomprise contacting the undesirable vegetation or locus thereof orapplying to the soil or water to prevent the emergence or growth ofvegetation with a compound of formula (I) or salt or ester thereof andnaptalam or salt or carboxylate salt or ester thereof, e.g.,sequentially or simultaneously. In some embodiments, the naptalam orsalt or carboxylate salt or ester thereof is applied at a rate fromabout 140 gai/ha to about 4,500 gai/ha and the compound of formula (I)of salt or ester thereof is applied at a rate from about 2 gae/ha toabout 300 gae/ha. In some embodiments, the naptalam or salt orcarboxylate salt or ester thereof is applied at a rate from about 30gai/ha to about 1,320 gai/ha and the compound of formula (I) of salt orester thereof is applied at a rate from about 8 gae/ha to about 32gae/ha. In certain embodiments, the methods utilize the compound offormula (I) or its benzyl or n-butyl ester and naptalam or salt orcarboxylate salt or ester thereof are used to control BRAPP, CYPRO,ECHCG ECHOR or FIMMI.

The components of the mixtures described herein can be applied eitherseparately or as part of a multipart herbicidal system.

The mixtures described herein can be applied in conjunction with one ormore other herbicides to control a wider variety of undesirablevegetation. When used in conjunction with other herbicides, thecomposition can be formulated with the other herbicide or herbicides,tank mixed with the other herbicide or herbicides or appliedsequentially with the other herbicide or herbicides. Some of theherbicides that can be employed in conjunction with the compositions andmethods described herein include, but are not limited to: 4-CPA; 4-CPB;4-CPP; 2,4-D; 2,4-D choline salt, 2,4-D esters and amines, 2,4-DB;3,4-DA; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB;acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor,alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin,amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid,amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron,asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne,barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin,benfuresate, bensulfuron-methyl, bensulide, benthiocarb,bentazon-sodium, benzadox, benzfendizone, benzipram, benzobicyclon,benzofenap, benzofluor, benzoylprop, benzthiazuron, bialaphos,bicyclopyrone, bifenox, bilanafos, bispyribac-sodium, borax, bromacil,bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon,butachlor, butafenacil, butamifos, butenachlor, buthidazole, buthiuron,butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrole,calcium chlorate, calcium cyanamide, cambendichlor, carbasulam,carbetamide, carboxazole chlorprocarb, carfentrazone-ethyl, CDEA, CEPC,chlomethoxyfen, chloramben, chloranocryl, chlorazifop, chlorazine,chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop,chlorflurazole, chloridazon, chlorimuron, chlornitrofen, chloropon,chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron,chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron,cisanilide, clethodim, cliodinate, clodinafop-propargyl, clofop,clomazone, clomeprop, cloprop, cloproxydim, clopyralid,cloransulam-methyl, CMA, copper sulfate, CPMF, CPPC, credazine, cresol,cumyluron, cyanatryn, cyanazine, cycloate, cyclopyrimorate,cyclosulfamuron, cycloxydim, cycluron, cyhalofop-butyl, cyperquat,cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor,desmedipham, desmetryn, di-allate, dicamba, dichlobenil, dichloralurea,dichlormate, dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam,diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat,diflufenican, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dimethenamid-P, dimexano, dimidazon, dinitramine,dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid,dipropetryn, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP,eglinazine, endothal, epronaz, EPTC, erbon, esprocarb, ethalfluralin,ethbenzamide, ethametsulfuron, ethidimuron, ethiolate, ethobenzamid,etobenzamid, ethofumesate, ethoxyfen, ethoxysulfuron, etinofen,etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop,fenoxaprop-P-ethyl, fenoxaprop-P-ethyl+isoxadifen-ethyl, fenoxasulfone,fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate,flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop,fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron,fluchloralin, flufenacet, flufenican, flufenpyr-ethyl, flumetsulam,flumezin, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron,fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron,flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone,fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurtamone,fluthiacet, fomesafen, foramsulfuron, fosamine, fumiclorac, furyloxyfen,glufosinate, glufosinate-ammonium, glufosinate-P-ammonium, glyphosatesalts and esters, halauxifen, halauxifen-methyl, halosafen,halosulfuron-methyl, haloxydine, haloxyfop-methyl, haloxyfop-P-methyl,hexachloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox,imazapic, imazapyr, imazaquin, imazosulfuron, imazethapyr, indanofan,indaziflam, iodobonil, iodomethane, iodosulfuron,iodosulfuron-ethyl-sodium, iofensulfuron, ioxynil, ipazine,ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin,isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben,isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox,lactofen, lenacil, linuron, MAA, MAMA, MCPA esters and amines,MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet,mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop,metamitron, metazachlor, metazosulfuron, metflurazon,methabenzthiazuron, methalpropalin, methazole, methiobencarb,methiozolin, methiuron, methometon, methoprotryne, methyl bromide,methyl isothiocyanate, methyldymron, metobenzuron, metobromuron,metolachlor, metosulam, metoxuron, metribuzin, metsulfuron,metsulfuron-methyl, molinate, monalide, monisouron, monochloroaceticacid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide,neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen,norflurazon, noruron, OCH, orbencarb, ortho-dichlorobenzene,orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon,oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl, parafluoron,paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam,pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid,phenisopham, phenmedipham, phenmedipham-ethyl, phenobenzuron,phenylmercury acetate, picloram, picolinafen, pinoxaden, piperophos,potassium arsenite, potassium azide, potassium cyanate, pretilachlor,primisulfuron-methyl, procyazine, prodiamine, profluazol, profluralin,profoxydim, proglinazine, prohexadione-calcium, prometon, prometryn,pronamide, propachlor, propanil, propaquizafop, propazine, propham,propisochlor, propoxycarbazone, propyrisulfuron, propyzamide,prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanon,pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate,pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor,pyridafol, pyridate, pyriftalid, pyriminobac, pyrimisulfan,pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac,quinoclamine, quinonamid, quizalofop, quizalofop-P-ethyl, rhodethanil,rimsulfuron, saflufenacil, S-metolachlor, sebuthylazine, secbumeton,sethoxydim, siduron, simazine, simeton, simetryn, SMA, sodium arsenite,sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone,sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapin,swep, SYN-523, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione,tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,terbuthylazine, terbutryn, tetrafluoron, thenylchlor, thiazafluoron,thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl,thifensulfuron, thifensulfurn-methyl, thiobencarb, tiocarbazil,tioclorim, topramezone, tralkoxydim, triafamone, tri-allate,triasulfuron, triaziflam, tribenuron, tribenuron-methyl, tricamba,triclopyr choline salt, triclopyr esters, amines, and salts, tridiphane,trietazine, trifloxysulfuron, trifluralin, triflusulfuron, trifop,trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritactritosulfuron, vernolate, xylachlor and salts, esters, optically activeisomers and mixtures thereof.

The compositions and methods described herein, can further be used inconjunction with glyphosate, 5-enolpyruvylshikimate-3-phosphate (EPSP)synthase inhibitors, glufosinate, glutamine synthetase inhibitors,dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxintransport inhibitors, aryloxyphenoxypropionates, cyclohexanediones,phenylpyrazolines, acetyl CoA carboxylase (ACCase) inhibitors,imidazolinones, sulfonylureas, pyrimidinylthiobenzoates,triazolopyrimidines, sulfonylaminocarbonyltriazolinones, acetolactatesynthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors,4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, phytoenedesaturase inhibitors, carotenoid biosynthesis inhibitors,protoporphyrinogen oxidase (PPO) inhibitors, cellulose biosynthesisinhibitors, mitosis inhibitors, microtubule inhibitors, very long chainfatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors,photosystem I inhibitors, photosystem II inhibitors, triazines, andbromoxynil on glyphosate-tolerant, EPSP synthase inhibitor-tolerant,glufosinate-tolerant, glutamine synthetase inhibitor-tolerant,dicamba-tolerant, phenoxy auxin-tolerant, pyridyloxy auxin-tolerant,auxin-tolerant, auxin transport inhibitor-tolerant,aryloxyphenoxypropionate-tolerant, cyclohexanedione-tolerant,phenylpyrazoline-tolerant, ACCase-tolerant, imidazolinone-tolerant,sulfonylurea-tolerant, pyrimidinylthiobenzoate-tolerant,triazolopyrimidine-tolerant, sulfonylaminocarbonyltriazolinone-tolerant,ALS- or AHAS-tolerant, HPPD-tolerant, phytoene desaturaseinhibitor-tolerant, carotenoid biosynthesis inhibitor tolerant,PPO-tolerant, cellulose biosynthesis inhibitor-tolerant, mitosisinhibitor-tolerant, microtubule inhibitor-tolerant, very long chainfatty acid inhibitor-tolerant, fatty acid and lipid biosynthesisinhibitor-tolerant, photosystem I inhibitor-tolerant, photosystem IIinhibitor-tolerant, triazine-tolerant, bromoxynil-tolerant, and cropspossessing multiple or stacked traits conferring tolerance to multiplechemistries and/or multiple modes of action via single and/or multipleresistance mechanisms. In some embodiments, the compound of formula (I)or salt or ester thereof and complementary herbicide or salt or esterthereof are used in combination with herbicides that are selective forthe crop being treated and which complement the spectrum of weedscontrolled by these compounds at the application rate employed. In someembodiments, the compositions described herein and other complementaryherbicides are applied at the same time, either as a combinationformulation or as a tank mix.

In some embodiments, the compositions described herein are employed incombination with one or more herbicide safeners, such as AD-67 (MON4660), benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl),cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton,fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole,harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi,mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), oxabetrinil,829148 and N-phenyl-sulfonylbenzoic acid amides, to enhance theirselectivity. In some embodiments, the safeners are employed in rice,cereal, corn, or maize settings. In some embodiments, the safener iscloquintocet or an ester or salt thereof. In certain embodiments,cloquintocet is utilized to antagonize harmful effects of thecompositions on rice and cereals. In some embodiments, the safener iscloquintocet (mexyl).

In some embodiments, the compositions described herein are employed incombination with one or more plant growth regulators, such as2,3,5-tri-iodobenzoic acid, IAA, IBA, naphthaleneacetamide,α-naphthaleneacetic acids, benzyladenine, 4-hydroxyphenethyl alcohol,kinetin, zeatin, endothal, ethephon, pentachlorophenol, thidiazuron,tribufos, aviglycine, ethephon, maleic hydrazide, gibberellins,gibberellic acid, abscisic acid, ancymidol, fosamine, glyphosine,isopyrimol, jasmonic acid, maleic hydrazide, mepiquat,2,3,5-tri-iodobenzoic acid, morphactins, dichlorflurenol, flurprimidol,mefluidide, paclobutrazol, tetcyclacis, uniconazole, brassinolide,brassinolide-ethyl, cycloheximide, ethylene, methasulfocarb,prohexadione, triapenthenol and trinexapac.

In some embodiments, the plant growth regulators are employed in one ormore crops or settings, such as rice, cereal crops, corn, maize,broadleaf crops, oilseed rape/canola, turf, pineapple, sugarcane,sunflower, pastures, grasslands, rangelands, fallowland, turf, tree andvine orchards, plantation crops, vegetables, and non-crop (ornamentals)settings. In some embodiments, the plant growth regulator is mixed withthe compound of formula (I), or mixed with the compound of formula (I)and auxin transport inhibitors to cause a preferentially advantageouseffect on plants.

In some embodiments, compositions provided herein further comprise atleast one agriculturally acceptable adjuvant or carrier. Suitableadjuvants or carriers should not be phytotoxic to valuable crops,particularly at the concentrations employed in applying the compositionsfor selective weed control in the presence of crops, and should notreact chemically with herbicidal components or other compositioningredients. Such mixtures can be designed for application directly toweeds or their locus or can be concentrates or formulations that arenormally diluted with additional carriers and adjuvants beforeapplication. They can be solids, such as, for example, dusts, granules,water-dispersible granules, or wettable powders, or liquids, such as,for example, emulsifiable concentrates, solutions, emulsions orsuspensions. They can also be provided as a pre-mix or tank mixed.

Suitable agricultural adjuvants and carriers include, but are notlimited to, crop oil concentrate; nonylphenol ethoxylate;benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleumhydrocarbon, alkyl esters, organic acid, and anionic surfactant; C₉-C₁₁alkylpolyglycoside; phosphated alcohol ethoxylate; natural primaryalcohol (C₁₂-C₁₆) ethoxylate; di-sec-butylphenol EO-PO block copolymer;polysiloxane-methyl cap; nonylphenol ethoxylate+urea ammonium nitrate;emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate(8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate-99.

Liquid carriers that can be employed include water and organic solvents.The organic solvents include, but are not limited to, petroleumfractions or hydrocarbons such as mineral oil, aromatic solvents,paraffinic oils, and the like; vegetable oils such as soybean oil,rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil,corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, saffloweroil, sesame oil, tung oil and the like; esters of the above vegetableoils; esters of monoalcohols or dihydric, trihydric, or other lowerpolyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate,n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octylsuccinate, di-butyl adipate, di-octyl phthalate and the like; esters ofmono, di and polycarboxylic acids and the like. Specific organicsolvents include, but are not limited to toluene, xylene, petroleumnaphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone,trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butylacetate, propylene glycol monomethyl ether and diethylene glycolmonomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amylalcohol, ethylene glycol, propylene glycol, glycerine,N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide,liquid fertilizers and the like. In certain embodiments, Water is thecarrier for the dilution of concentrates.

Suitable solid carriers include but are not limited to talc,pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr,chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay,Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice,wood flour, walnut shell flour, lignin, cellulose, and the like.

In some embodiments, the compositions described herein further compriseone or more surface-active agents. In some embodiments, suchsurface-active agents are employed in both solid and liquidcompositions, and in certain embodiments those designed to be dilutedwith carrier before application. The surface-active agents can beanionic, cationic or nonionic in character and can be employed asemulsifying agents, wetting agents, suspending agents, or for otherpurposes. Surfactants which may also be used in the present formulationsare described, inter alia, in “McCutcheon's Detergents and EmulsifiersAnnual,” MC Publishing Corp., Ridgewood, N.J., 1998 and in “Encyclopediaof Surfactants,” Vol. I-III, Chemical Publishing Co., New York, 1980-81.Surface-active agents include, but are not limited to salts of alkylsulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonatesalts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkyleneoxide addition products, such as nonylphenol-C₁₈ ethoxylate;alcohol-alkylene oxide addition products, such as tridecyl alcohol-C₁₆ethoxylate; soaps, such as sodium stearate; alkyl-naphthalene-sulfonatesalts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters ofsulfosuccinate salts, such as sodium di(2-ethylhexyl)sulfosuccinate;sorbitol esters, such as sorbitol oleate; quaternary amines, such aslauryl trimethylammonium chloride; polyethylene glycol esters of fattyacids, such as polyethylene glycol stearate; block copolymers ofethylene oxide and propylene oxide; salts of mono and dialkyl phosphateesters; vegetable or seed oils such as soybean oil, rapeseed/canola oil,olive oil, castor oil, sunflower seed oil, coconut oil, corn oil,cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesameoil, tung oil and the like; and esters of the above vegetable oils, andin certain embodiments, methyl esters.

In some embodiments, these materials, such as vegetable or seed oils andtheir esters, can be used interchangeably as an agricultural adjuvant,as a liquid carrier or as a surface active agent.

Other exemplary additives for use in the compositions provided hereininclude but are not limited to compatibilizing agents, antifoam agents,sequestering agents, neutralizing agents and buffers, corrosioninhibitors, dyes, odorants, spreading agents, penetration aids, stickingagents, dispersing agents, thickening agents, freezing pointdepressants, antimicrobial agents, and the like. The compositions mayalso contain other compatible components, for example, other herbicides,plant growth regulants, fungicides, insecticides, and the like and canbe formulated with liquid fertilizers or solid, particulate fertilizercarriers such as ammonium nitrate, urea and the like.

In some embodiments, the concentration of the active ingredients in thecompositions described herein is from about 0.0005 to 98 percent byweight. In some embodiments, the concentration is from about 0.0006 to90 percent by weight. In compositions designed to be employed asconcentrates, the active ingredients, in certain embodiments, arepresent in a concentration from about 0.1 to 98 weight percent, and incertain embodiment's about 0.5 to 90 weight percent. Such compositionsare, in certain embodiments, diluted with an inert carrier, such aswater, before application. The diluted compositions usually applied toweeds or the locus of weeds contain, in certain embodiments, about0.0006 to 3.0 weight percent active ingredient and in certainembodiments contain about 0.01 to 1.0 weight percent.

The present compositions can be applied to weeds or their locus by theuse of conventional ground or aerial dusters, sprayers, and granuleapplicators, by addition to irrigation or paddy water, and by otherconventional means known to those skilled in the art.

The described embodiments and following examples are for illustrativepurposes and are not intended to limit the scope of the claims. Othermodifications, uses, or combinations with respect to the compositionsdescribed herein will be apparent to a person of ordinary skill in theart without departing from the spirit and scope of the claimed subjectmatter.

EXAMPLES

Results in Examples I and II are greenhouse trial results.

Example I Evaluation of Postemergence Foliar-Applied Herbicidal Mixturesfor Weed Control in Direct Seeded Rice

Seeds or nutlets of the desired test plant species were planted in asoil matrix prepared by mixing a loam or sandy loam soil (e.g., 28.6percent silt, 18.8 percent clay, and 52.6 percent sand, with a pH ofabout 5.8 and an organic matter content of about 1.8 percent) andcalcareous grit in an 80 to 20 ratio. The soil matrix was contained inplastic pots with a volume of 1 quart and a surface area of 83.6 squarecentimeters (cm²). When required to ensure good germination and healthyplants, a fungicide treatment and/or other chemical or physicaltreatment was applied. The plants were grown for 8-22 days in agreenhouse with an approximate 14 h photoperiod which was maintained atabout 29° C. during the day and 26° C. during the night. Nutrients(Peters Excel® 15-5-15 5-Ca 2-Mg and iron chelate) were applied in theirrigation solution as needed and water was added on a regular basis.Supplemental lighting was provided with overhead metal halide 1000-Wattlamps as necessary. The plants were employed for testing when theyreached the first through fourth true leaf stage.

Treatments consisted of the acid or esters of4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylicacid (Compound A), each formulated as an SC (suspension concentrate),and various herbicidal components alone and in combination. Forms ofcompound A were applied on an acid equivalent basis.

Forms of compound A (compound of formula I) tested include:

Other herbicidal components were applied on an active ingredient basisand included auxin transport inhibiting (ATI) herbicides chlorflurenol(technical material), chlorflurenol-methyl (technical material),diflufenzopyr (technical material), diflufenzopyr sodium (technicalmaterial), flurenol-methyl (technical material) and naptalam (technicalmaterial).

Treatment requirements were calculated based upon the rates beingtested, the concentration of active ingredient or acid equivalent in theformulation, and a 12 mL application volume at a rate of 187 L/ha.

For treatments comprised of formulated compounds, measured amounts ofcompounds can be placed individually in 25 mL glass vials and diluted ina volume of 1.25% (v/v) Agri-Dex® crop oil concentrated to obtain 12×stock solutions. If a test compound does not dissolve readily, themixture can be warmed and/or sonicated. Application solutions can beprepared by adding an appropriate amount of each stock solution (e.g., 1mL) and diluted to the appropriate final concentrations with theaddition of 10 mL of an aqueous mixture of 1.25% (v/v) crop oilconcentrate so that the final spray solutions contain 1.25+/−0.05% (v/v)crop oil concentrate.

For treatments comprised of technical compounds, weighed amounts can beplaced individually in 25 mL glass vials and dissolved in a volume of97:3 v/v acetone/DMSO to obtain 12× stock solutions. If a test compounddoes not dissolve readily, the mixture can be warmed and/or sonicated.Application solutions can be prepared by adding an appropriate amount ofeach stock solution (e.g., 1 mL) and diluted to the appropriate finalconcentrations with the addition of 10 mL of an aqueous mixture of 1.5%(v/v) crop oil concentrate so that the final spray solutions contain1.25% (v/v) crop oil concentrate. When technical materials are used, theconcentrated stock solutions can be added to the spray solutions so thatthe final acetone and DMSO concentrations of the application solutionsare 16.2% and 0.5%, respectively.

For treatments comprised of formulated and technical compounds, weighedamounts of the technical materials were placed individually in 25 mLglass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain12× stock solutions, and measured amounts of the formulated compoundswere placed individually in 25 mL glass vials and diluted in a volume of1.5% (v/v) crop oil concentrate or water to obtain 12× stock solutions.If a test compound did not dissolve readily, the mixture was warmedand/or sonicated. Application solutions were prepared by adding anappropriate amount of each stock solution (e.g., 1 mL) and diluted tothe appropriate final concentrations with the addition of an appropriateamount of an aqueous mixture of 1.5% (v/v) crop oil concentrate so thatthe final spray solutions contained 1.25% (v/v) crop oil concentrate.When required, additional water and/or 97:3 v/v acetone/DMSO was addedto individual application solutions so that the final acetone and DMSOconcentrations of the application solutions being compared were 8.1% and0.25%, respectively.

All stock solutions and applications solutions were visually inspectedfor compound compatibility prior to application. Spray solutions wereapplied to the plant material with an overhead Mandel track sprayerequipped with an 8002E nozzle calibrated to deliver 187 L/ha over anapplication area of 0.503 m² at a spray height of 18 to 20 inches (46 to50 cm) above average plant canopy height. Control plants were sprayed inthe same manner with the solvent blank.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After approximately 3 weeks, the condition of the testplants as compared with that of the untreated plants was determinedvisually and scored on a scale of 0 to 100 percent where 0 correspondsto no injury or growth inhibition and 100 corresponds to complete kill.

Colby's equation was used to determine the herbicidal effects expectedfrom the mixtures (Colby, S. R. 1967. Calculation of the synergistic andantagonistic response of herbicide combinations. Weeds 15:20-22.).

The following equation was used to calculate the expected activity ofmixtures containing two active ingredients, A and B:Expected=A+B−(A×B/100)

A=observed efficacy of active ingredient A at the same concentration asused in the mixture.

B=observed efficacy of active ingredient B at the same concentration asused in the mixture.

The compounds tested, application rates employed, plant species tested,and results are given in Tables 1-6.

TABLE 1 Synergistic Activity of Foliar-Applied Compound A Acid andChlorflurenol-Methyl Ester Herbicidal Compositions on Control of WeedsCommon to Rice Cropping Systems. Compound Chlorflurenol- Visual WeedControl (%) - 20 DAA A Acid Methyl ECHCG gae/ha gai/ha Obs Exp 4.38 0 60— 8.75 0 80 — 0 275 0 — 4.38 275 99 60 8.75 275 95 80 CompoundChlorflurenol- Visual Weed Control (%) - 20 DAA A Acid Methyl ECHCOCYPIR gae/ha gai/ha Obs Exp Obs Exp 4.38 0 40 — 30 — 0 68.75 0 — 0 — 0137.5 0 — 0 — 0 275 0 — 0 — 4.38 68.75 90 40 60 30 4.38 137.5 90 40 6030 4.38 275 90 40 99 30 Compound Chlorflurenol- Visual Weed Control(%) - 20 DAA A Acid Methyl LEFCH IPOHE gae/ha gai/ha Obs Exp Obs Exp4.38 0 0 — 20 — 8.75 0 30 — 20 — 17.5 0 30 — 50 — 0 275 10 — 55 — 4.38275 55 10 85 64 8.75 275 50 37 80 64 17.5 275 50 37 80 78

TABLE 2 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Chlorflurenol-Methyl Herbicidal Compositions on Control of WeedsCommon to Rice Cropping Systems. Compound A Benzyl Chlorflurenol- VisualWeed Control (%) - 20 DAA Ester Methyl DIGSA gae/ha gai/ha Obs Exp 4.380 40 — 8.75 0 40 — 0 68.75 0 — 0 137.5 0 — 0 275 0 — 4.38 68.75 25 408.75 68.75 60 40 4.38 137.5 60 40 8.75 137.5 60 40 4.38 275 40 40 8.75275 85 40 Compound A Benzyl Chlorflurenol- Visual Weed Control (%) - 20DAA Ester Methyl ECHCG CYPIR gae/ha gai/ha Obs Exp Obs Exp 4.38 0 60 —70 — 0 68.75 0 — 0 — 0 137.5 0 — 0 — 0 275 0 — 0 — 4.38 68.75 80 60 9570 4.38 137.5 90 60 80 70 4.38 275 85 60 100 70 Compound A BenzylChlorflurenol- Visual Weed Control (%) - 20 DAA Ester Methyl ECHCO IPOHEgae/ha gai/ha Obs Exp Obs Exp 4.38 0 60 — 10 — 8.75 0 80 — 15 — 0 137.50 — 50 — 0 275 0 — 55 — 4.38 137.5 80 60 75 55 8.75 137.5 95 80 70 584.38 275 85 60 85 60 8.75 275 99 80 85 62 Compound A BenzylChlorflurenol- Visual Weed Control (%) - 20 DAA Ester Methyl LEFCHgae/ha gai/ha Obs Exp 4.38 0 15 — 8.75 0 30 — 0 68.75 0 — 0 137.5 10 — 0275 10 — 4.38 68.75 50 15 8.75 68.75 55 30 4.38 137.5 30 24 8.75 137.555 37 4.38 275 75 24 8.75 275 45 37

TABLE 3 Synergistic Activity of Foliar-Applied Compound A Acid andDiflufenzopyr Herbicidal Compositions on Control of Weeds Common to RiceCropping Systems. Compound Visual Weed Control (%) - 21 DAA A AcidDiflufenzopyr BRAPP gae/ha gai/ha Obs Exp 8.75 0 60 — 0 8.75 0 — 0 17.540 — 0 35 80 — 8.75 8.75 95 60 8.75 17.5 90 76 8.75 35 95 92 CompoundVisual Weed Control (%) - 21 DAA A Acid Diflufenzopyr ECHCO gae/hagai/ha Obs Exp 4.38 0 60 — 0 8.75 30 — 0 17.5 30 — 0 35 40 — 4.38 8.7595 72 4.38 17.5 95 72 4.38 35 95 76 Compound Visual Weed Control (%) -21 DAA A Acid Diflufenzopyr LEFCH gae/ha gai/ha Obs Exp 8.75 0 30 — 17.50 30 — 0 8.75 0 — 0 17.5 10 — 8.75 8.75 15 30 17.5 8.75 50 30 8.75 17.550 37 17.5 17.5 65 37

TABLE 4 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Diflufenzopyr Herbicidal Compositions on Control of Weeds Common toRice Cropping Systems. Compound A Benzyl Visual Weed Control (%) - 21DAA Ester Diflufenzopyr BRAPP gae/ha gai/ha Obs Exp 4.38 0 70 — 8.75 075 — 17.5 0 95 — 0 8.75 0 — 4.38 8.75 95 70 8.75 8.75 95 75 17.5 8.75 9595 Compound A Benzyl Visual Weed Control (%) - 21 DAA EsterDiflufenzopyr DIGSA gae/ha gai/ha Obs Exp 17.5 0 30 — 0 17.5 10 — 0 3520 — 17.5 17.5 80 37 17.5 35 80 44 Compound A Benzyl Visual Weed Control(%) - 21 DAA Ester Diflufenzopyr LEFCH IPOHE gae/ha gai/ha Obs Exp ObsExp 4.38 0 15 — 10 — 8.75 0 40 — 10 — 17.5 0 50 — 25 — 0 8.75 0 — 75 — 017.5 10 — 70 — 4.38 8.75 15 15 85 78 8.75 8.75 50 40 85 78 17.5 8.75 6550 90 81 4.38 17.5 50 24 85 73 8.75 17.5 55 46 85 73 17.5 17.5 60 55 8578

TABLE 5 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Flurenol-methyl Herbicidal Compositions on Control of Weeds Commonto Rice Cropping Systems. Compound A Benzyl Flurenol- Visual WeedControl (%) - 22 DAA Ester methyl BRAPP CYPIR gae/ha gai/ha Obs Exp ObsExp 8 0 35 — 30 — 0 68.75 0 — 0 — 0 137.5 0 — 0 — 0 275 30 — 60 — 868.75 70 35 65 30 8 137.5 80 35 75 30 8 275 75 55 65 72

TABLE 6 Synergistic Activity of Foliar-Applied Compound A Benzyl Esterand Naptalam Herbicidal Compositions on Control of Weeds Common to RiceCropping Systems. Compound A Benzyl Visual Weed Control (%) - 22 DAAEster Naptalam BRAPP gae/ha gai/ha Obs Exp 8 0 35 — 16 0 80 — 0 30 0 — 060 0 — 0 120 0 — 8 30 75 35 16 30 80 80 8 60 70 35 16 60 90 80 8 120 8035 16 120 85 80 Compound A Benzyl Visual Weed Control (%) - 22 DAA EsterNaptalam LEFCH gae/ha gai/ha Obs Exp 32 0 40 — 0 60 15 — 0 120 15 — 3260 60 49 32 120 60 49 Compound A Benzyl Visual Weed Control (%) - 22 DAAEster Naptalam IPOHE gae/ha gai/ha Obs Exp 8 0 0 — 16 0 25 — 32 0 50 — 060 15 — 0 120 15 — 8 60 25 15 16 60 45 36 32 60 60 58 8 120 40 15 16 12025 36 32 120 70 58 BRAPP Brachiaria platyphylla (Griseb.) Nashsignalgrass, broadleaf CYPIR Cyperus iria L. flatsedge, rice DIGSADigitaria sanguinalis (L.) Scop. crabgrass, large ECHCG Echinochloacrusgalli (L.) Beauv. barnyardgrass ECHCO Echinochloa colona (L.) Linkjunglerice IPOHE Ipomoea hederacea Jacq. morningglory, ivyleaf LEFCHLeptochloa chinensis (L.) Nees sprangletop, Chinese gae/ha = grams acidequivalent per hectare gai/ha = grams active ingredient per hectare Obs= observed value Exp = expected value as calculated by Colby's equationDAA = days after application

Example II Evaluation of In-Water Applied Herbicidal Mixtures for WeedControl in Transplanted Paddy Rice

Weed seeds or nutlets of the desired test plant species were planted inpuddled soil (mud) prepared by mixing a shredded, non-sterilized mineralsoil (50.5 percent silt, 25.5 percent clay, and 24 percent sand, with apH of about 7.6 and an organic matter content of about 2.9 percent) andwater at a 1:1 volumetric ratio. The prepared mud was dispensed in 365mL aliquots into 16-ounce (oz.) non-perforated plastic pots with asurface area of 86.59 square centimeters (cm²) leaving a headspace of 3centimeters (cm) in each pot. Mud was allowed to dry overnight prior toplanting or transplanting. Rice seeds were planted in Sun Gro MetroMix®306 planting mixture, which typically has a pH of 6.0 to 6.8 and anorganic matter content of about 30 percent, in plastic plug trays.Seedlings at the second or third leaf stage of growth were transplantedinto 840 mL of mud contained in 32-oz. non-perforated plastic pots witha surface area of 86.59 cm² 4 days prior to herbicide application. Thepaddy was created by filling the headspace of the pots with 2.5 to 3 cmof water. When required to ensure good germination and healthy plants, afungicide treatment and/or other chemical or physical treatment wasapplied. The plants were grown for 4-22 days in a greenhouse with anapproximate 14 h photoperiod which was maintained at about 29′C duringthe day and 26° C. during the night. Nutrients were added as Osmocote®(19:6:12, N:P:K+minor nutrients) at 2 g per 16-oz. pot and 4 g per960-mL 32-oz. pot. Water was added on a regular basis to maintain thepaddy flood, and supplemental lighting was provided with overhead metalhalide 1000-Watt lamps as necessary. The plants were employed fortesting when they reached the second or third true leaf stage.

Treatments consisted of the acid or esters of4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylicacid (compound A) each formulated as an SC and various herbicidalcomponents alone and in combination. Forms of compound A were applied onan acid equivalent basis.

Forms of compound A (compound of formula I) tested include:

Other herbicidal components were applied on an active ingredient basisand included auxin transport inhibiting (ATI) herbicideschlorflurenol-methyl (technical material), chlorflurenol (technicalmaterial), diflufenzopyr (technical material), dilfufenzopyr sodium(technical material), flurenol-methyl (technical material), and naptalam(technical material).

Treatment requirements for each compound or herbicidal component werecalculated based upon the rates being tested, the concentration ofactive ingredient or acid equivalent in the formulation, an applicationvolume of 2 mL per component per pot, and an application area of 86.59cm² per pot.

For formulated compounds, a measured amount was placed in an individual100 or 200 mL glass vial and was dissolved in a volume of 1.25% (v/v)Agri-Dex® crop oil concentrate to obtain application solutions. If thetest compound did not dissolve readily, the mixture was warmed and/orsonicated.

For technical grade compounds, a weighed amount was placed in anindividual 100 to 200 mL glass vial and was dissolved in a volume ofacetone to obtain concentrated stock solutions. If the test compound didnot dissolve readily, the mixture was warmed and/or sonicated. Theconcentrated stock solutions obtained were diluted with an equivalentvolume of an aqueous mixture containing 2.5% (v/v) crop oil concentrateso that the final application solutions contained 1.25% (v/v) crop oilconcentrate.

Applications were made by injecting with a pipetter appropriate amountsof the application solutions, individually and sequentially, into theaqueous layer of the paddy. Control plants were treated in the samemanner with the solvent blank. Applications were made so that alltreated plant material received the same concentrations of acetone andcrop oil concentrate.

The treated plants and control plants were placed in a greenhouse asdescribed above and water was added as needed to maintain a paddy flood.After approximately 3 weeks the condition of the test plants as comparedwith that of the untreated plants was determined visually and scored ona scale of 0 to 100 percent where 0 corresponds to no injury or growthinhibition and 100 corresponds to complete kill.

Colby's equation was used to determine the herbicidal effects expectedfrom the mixtures (Colby, S. R. 1967. Calculation of the synergistic andantagonistic response of herbicide combinations. Weeds 15:20-22.).

The following equation was used to calculate the expected activity ofmixtures containing two active ingredients, A and B:Expected=A+B−(A×B/100)

A=observed efficacy of active ingredient A at the same concentration asused in the mixture.

B=observed efficacy of active ingredient B at the same concentration asused in the mixture.

Some of the compounds tested, application rates employed, plant speciestested, and results are given in Tables 7-13.

TABLE 7 Synergistic Activity of In-Water Applications of Compound A Acidand Chlorflurenol-Methyl Herbicidal Compositions on Control of WeedsCommon to Rice Cropping Systems. Visual Weed Control (%) - CompoundChlorflurenol- 20 DAA A Acid Methyl ECHCG gae/ha gai/ha Obs Exp   17.5 050 — 35 0 95 —  0 275 15 —  0 550 20 —   17.5 275 100 58 35 275 100 96  17.5 550 100 60 35 550 100 96 Compound Chlorflurenol- Visual WeedControl (%) - 20 DAA A Acid Methyl ECHOR LEFCH SCPMA gae/ha gai/ha ObsExp Obs Exp Obs Exp 8.75 0 10 — 20 — 0 — 17.5 0 15 — 0 — 0 — 35 0 25 —30 — 30 — 0 550 10 — 0 — 80 — 8.75 550 60 19 40 20 100 80 17.5 550 50 2440  0 100 80 35 550 70 33 30 30 100 86

TABLE 8 Synergistic Activity of In-Water Applications of Compound ABenzyl Ester and Chlorflurenol-Methyl Herbicidal Compositions on Controlof Weeds Common to Rice Cropping Systems. Compound A BenzylChlorflurenol- Visual Weed Control (%) - 20 DAA Ester Methyl ECHCGgae/ha gai/ha Obs Exp 4.38 0 40 — 0 275 15 — 0 550 20 — 4.38 275 100 494.38 550 99 52 Compound A Benzyl Chlorflurenol- Visual Weed Control(%) - 20 DAA Ester Methyl ECHOR gae/ha gai/ha Obs Exp 4.38 0 10 — 8.75 015 — 0 275 20 — 0 550 10 — 4.38 275 80 28 8.75 275 60 32 4.38 550 55 198.75 550 80 24 Compound A Benzyl Chlorflurenol- Visual Weed Control(%) - 20 DAA Ester Methyl LEFCH gae/ha gai/ha Obs Exp 4.38 0 0 — 8.75 020 — 17.5 0 30 — 0 275 0 — 0 550 0 — 4.38 275 30 0 8.75 275 30 20 17.5275 50 30 4.38 550 100 0 8.75 550 90 20 17.5 550 95 30 Compound A BenzylChlorflurenol- Visual Weed Control (%) - 20 DAA Ester Methyl SCPMAgae/ha gai/ha Obs Exp 4.38 0 0 — 8.75 0 0 — 17.5 0 0 — 0 275 75 — 4.38275 95 75 8.75 275 100 75 17.5 275 95 75

TABLE 9 Synergistic Activity of In-Water Applications of Compound A Acidand Chlorflurenol Herbicidal Compositions on Control of Weeds Common toRice Cropping Systems. Compound Visual Weed Control (%) - 22 DAA A AcidChlorflurenol ECHOR gae/ha gai/ha Obs Exp 8.75 0 0 — 17.5 0 20 — 35 0 20— 0 550 30 — 8.75 550 40 30 17.5 550 40 44 35 550 70 44 Compound VisualWeed Control (%) - 22 DAA A Acid Chlorflurenol ECHCG SCPMA gae/ha gai/haObs Exp Obs Exp 8.75 0 0 — 0 — 17.5 0 15 — 0 — 35 0 15 — 0 — 0 275 10 —45 — 8.75 275 20 10 50 45 17.5 275 15 24 70 45 35 275 40 24 50 45

TABLE 10 Synergistic Activity of In-Water Applications of Compound ABenzyl Ester and Chlorflurenol Herbicidal Compositions on Weed Controlin a Rice Cropping System. Compound A Benzyl Visual Weed Control (%) -22 DAA Ester Chlorflurenol ECHCG gae/ha gai/ha Obs Exp 4.38 0 10 — 8.750 25 — 17.5 0 60 — 0 275 10 — 4.38 275 40 19 8.75 275 35 33 17.5 275 8564 Compound A Benzyl Visual Weed Control (%) - 22 DAA EsterChlorflurenol SCPMA gae/ha gai/ha Obs Exp 8.75 0 0 — 17.5 0 0 — 0 275 45— 0 550 60 — 8.75 275 60 45 17.5 275 60 45 8.75 550 50 60 17.5 550 80 60

TABLE 11 Synergistic Activity of In-Water Applications of Compound ABenzyl Ester and Diflufenzopyr Sodium Herbicidal Compositions on WeedControl in a Rice Cropping System. Compound A Benzyl DiflufenzopyrVisual Weed Control (%) - 19 DAA Ester sodium ECHCG CYPRO gae/ha gai/haObs Exp Obs Exp 8 0 30 — 50 — 16 0 20 — 85 — 32 0 40 — 90 — 0 17.5 20 —0 — 0 35 50 — 0 — 0 70 20 — 10 — 8 17.5 50 44 70 50 16 17.5 95 36 85 8532 17.5 99 52 100 90 8 35 50 65 100 50 16 35 80 60 100 85 32 35 70 70100 90 8 70 75 44 85 55 16 70 90 36 80 87 32 70 99 52 100 91 Compound ABenzyl Diflufenzopyr Visual Weed Control (%) - 19 DAA Ester sodium FIMMIgae/ha gai/ha Obs Exp 16 0 0 — 0 17.5 50 — 0 35 55 — 0 70 60 — 16 17.575 50 16 35 75 55 16 70 75 60

TABLE 12 Synergistic Activity of In-Water Applications of Compound ABenzyl Ester and Flurenol-methyl Ester Herbicidal Compositions on WeedControl in a Rice Cropping System. Compound A Benzyl Flurenol- VisualWeed Control (%) - 19 DAA Ester methyl ECHCG FIMMI gae/ha gai/ha Obs ExpObs Exp 8 0 30 — 0 — 16 0 20 — 0 — 32 0 40 — 85 — 0 68.75 0 — 0 — 0137.5 0 — 0 — 0 275 0 — 20 — 8 68.75 35 30 0 0 16 68.75 20 20 20 0 3268.75 100 40 90 85 8 137.5 30 30 10 0 16 137.5 20 20 20 0 32 137.5 80 40100 85 8 275 95 30 35 20 16 275 85 20 85 20 32 275 100 40 100 88Compound A Benzyl Flurenol- Visual Weed Control (%) - 19 DAA Estermethyl CYPRO gae/ha gai/ha Obs Exp 8 0 50 — 16 0 85 — 32 0 90 — 0 68.750 — 0 137.5 0 — 8 68.75 85 50 16 68.75 80 85 32 68.75 100 90 8 137.5 8550 16 137.5 100 85 32 137.5 100 90

TABLE 13 Synergistic Activity of In-Water Applications of Compound ABenzyl Ester and Naptalam Herbicidal Compositions on Weed Control in aRice Cropping System. Compound A Benzyl Visual Weed Control (%) - 19 DAAEster Naptalam ECHCG FIMMI gae/ha gai/ha Obs Exp Obs Exp 8 0 30 — 0 — 160 20 — 0 — 32 0 40 — 85 — 0 330 20 — 50 — 8 330 95 44 65 50 16 330 85 3680 50 32 330 95 52 90 93 Compound A Benzyl Visual Weed Control (%) - 19DAA Ester Naptalam ECHOR gae/ha gai/ha Obs Exp 32 0 25 — 0 330 20 — 0660 25 — 0 1320 30 — 32 330 60 40 32 660 20 44 32 1320 70 48 Compound ABenzyl Visual Weed Control (%) - 19 DAA Ester Naptalam CYPRO gae/hagai/ha Obs Exp 8 0 50 — 16 0 85 — 32 0 90 — 0 330 0 — 0 1320 50 — 8 33090 50 16 330 85 85 32 330 100 90 8 1320 90 75 16 1320 100 93 32 1320 10095 CYPRO Cyperus rotundus L. nutsedge, purple ECHCG Echinochloacrusgalli (L.) Beauv. barnyardgrass ECHOR Echinochloa oryzoides (Ard.)Fritsch watergrass, early FIMMI Fimbristylis miliacea (L.) Vahlfringerush, globe LEFCH Leptochloa chinensis (L.) Nees sprangletop,Chinese SCPMA Schoenoplectus maritimus (L.) Lye or clubrush, seaBolboschoenus maritimus (L.) Palla gae/ha = grams acid equivalent perhectare gai/ha = grams active ingredient per hectare Obs = observedvalue Exp = expected value as calculated by Colby's equation DAA = daysafter application

What is claimed is:
 1. A herbicidal composition comprising aherbicidally effective amount of (a) a compound of the formula (I):

or a carboxylic acid, a carboxylate salt, an alkyl ester, anunsubstituted benzyl, a substituted benzyl, a C₁₋₄ alkyl, or an n-butylester, or an agriculturally acceptable salt of formula (I); and (b) atleast one herbicide selected from the group consisting ofchlorflurenol-methyl, chlorflurenol, diflufenzopyr, diflufenzopyrsodium, flurenol-methyl, flurenol, naptalam and agriculturallyacceptable carboxylate salts, carboxylic acids, or esters thereof,wherein (a) and (b) are present in the composition in a ratio such thatthe composition exhibits synergy.
 2. The composition of claim 1, whereinthe weight ratio given in units of gae/ha to gai/ha of the compound offormula (I) or agriculturally acceptable salt or ester thereof tochlorflurenol-methyl or chlorfluernol or agriculturally acceptablecarboxylate salt, carboxylic acid, or ester thereof is from about 1:3.9to about 1:125.6.
 3. The composition of claim 1, wherein the weightratio given in units of gae/ha to gai/ha of the compound of formula (I)or agriculturally acceptable salt or ester thereof to diflufenzopyr ordiflufenzopyr sodium or agriculturally acceptable salt or ester thereofis from about 2:1 to about 1:18.
 4. The composition of claim 1, whereinthe weight ratio given in units of gae/ha to gai/ha of compound offormula (I) or agriculturally acceptable salt or ester thereof toflurenol-methyl or flurenol or agriculturally acceptable salt or esterthereof is from about 1:2.2 to about 1:34.4.
 5. The composition of claim1, wherein the weight ratio given in units of gae/ha to gai/ha ofcompound of formula (I) or agriculturally acceptable salt or esterthereof to naptalam or agriculturally acceptable salt or ester thereofis from about 1:1 to about 1:165.
 6. The composition claim 1 furthercomprising an agriculturally acceptable adjuvant, carrier, or safener.7. A method of controlling undesirable vegetation, comprising the stepsof: contacting a plant, wherein the plant is undesirable vegetation, orthe locus thereof, or soil, or water, wherein the soil or the waterallows for the growth of the undesirable vegetation, with a herbicidallyeffective amount of a combination comprising (a) a compound of theformula (I):

or a carboxylic acid, a carboxylate salt, an alkyl ester, anunsubstituted benzyl, a substituted benzyl, a C₁₋₄ alkyl, or an n-butylester, or an agriculturally acceptable salt of formula (I); and (b) atleast one herbicide selected from the group consisting ofchlorflurenol-methyl, chlorflurenol, diflufenzopyr, diflufenzopyrsodium, flurenol-methyl, flurenol, naptalam and agriculturallyacceptable carboxylate salts, carboxylic acids, or esters thereof,wherein (a) and (b) are present in the combination in a ratio such thatthe combination exhibits synergy for the control of undesirablevegetation in a crop selected from the group consisting of rice,cereals, wheat, barley, oats, rye, sorghum, and corn/maize.
 8. Themethod of claim 7, wherein the water is part of a flooded rice paddy. 9.The method of claim 7, wherein the herbicidally effective amount of (a)is applied either pre- or post emergently to at least one of thefollowing: a crop, a field, or a paddy.
 10. The method of claim 7,wherein the undesirable vegetation is controlled in glyphosate-,5-enolpyruvylshikimate-3-phosphate synthase inhibitor-, glufosinate-,glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-, pyridyloxyauxin-, synthetic auxin-, auxin transport inhibitor-,aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetylCoA carboxylase inhibitor-, imidazolinone-, sulfonylurea-,pyrimidinylthiobenzoate-, triazolopyrimidine-,sulfonylaminocarbonyltriazolinone-, acetolactate synthase oracetohydroxy acid synthase inhibitor-, 4-hydroxyphenyl-pyruvatedioxygenase inhibitor-, phytoene desaturase inhibitor-, carotenoidbiosynthesis inhibitor-, protoporphyrinogen oxidase inhibitor-,cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubuleinhibitor-, long chain fatty acid inhibitor-, fatty acid and lipidbiosynthesis inhibitor-, photosystem I inhibitor-, photosystem IIinhibitor-, triazine-, or bromoxynil-tolerant crops.
 11. The method ofclaim 10, wherein a plant that is tolerant to at least one herbicide istreated, and wherein the tolerant plant is selected from the groupconsisting of crop plants that possesses multiple or stacked traitsconferring tolerance to multiple herbicides, and undesirable plants thatpossesses multiple or stacked traits conferring tolerance to multipleherbicides.
 12. The method of claim 11, wherein the plant that istolerant to at least one herbicide is resistant or tolerant toacetolactate synthase or acetohydroxy acid synthase inhibitors,photosystem II inhibitors, acetyl CoA carboxylase inhibitors, syntheticauxins, auxin transport inhibitors, photosystem I inhibitors,5-enolpyruvylshikimate-3-phosphate synthase inhibitors, microtubuleassembly inhibitors, fatty acid and lipid synthesis inhibitors,protoporphyrinogen oxidase inhibitors, carotenoid biosynthesisinhibitors, long chain fatty acid inhibitors, phytoene desaturaseinhibitors, glutamine synthetase inhibitors,4-hydroxyphenyl-pyruvate-dioxygenase inhibitors, mitosis inhibitors,cellulose biosynthesis inhibitors, herbicides with multiplemodes-of-action, quinclorac, arylaminopropionic acids, difenzoquat,endothall, or organoarsenicals.
 13. The method according to claim 7,wherein the amount of chlorflurenol-methyl or chlorflurenol is appliedat a rate, expressed in ai/ha of chlorflurenol-methyl or chlorflurenol,from about 68.75 to about
 550. 14. The method according to claim 9,wherein the wherein the controlled plant is at least one plant selectedfrom the genera consisting of: Echinochloa, Cyperus, Leptochloa,Ipomoea, Digitaria, Schoenoplectus, and Bolboschoenus.
 15. The methodaccording to claim 7, wherein the amount of diflufenzopyr ordiflufenzopyr sodium is applied at a rate, expressed in ai/ha ofdiflufenzopyr or diflufenzopyr sodium, from about 8.75 to about
 70. 16.The method according to claim 11, wherein the wherein the controlledplant is at least one plant selected from the genera consisting of:Brachiaria, Leptochloa, Digitaria, Ipomoea, Echinochloa, Cyperus, andFimbristylis.
 17. The method according to claim 7, wherein the amount offlurenol or flurenol-methyl is applied at a rate, expressed in ai/ha offlurenol or flurenol-methyl, from about 68.75 to about
 275. 18. Themethod according to claim 12, wherein the wherein the controlled plantis at least one plant selected from the genera consisting of:Brachiaria, Cyperus, Echinochloa, Fimbristylis, and Cyperus.
 19. Themethod according to claim 7, wherein the amount of naptalam is appliedat a rate, expressed in ai/ha of naptalam, from about 30 to about 1320.20. The method according to claim 14, wherein the wherein the controlledplant is at least one plant selected from the genera consisting of:Brachiaria, Leptochloa, Ipomoea, Echinochloa, Fimbristylis, Echinochloa,and Cyperus.